KR101561390B1 - 3,6―안하이드로―l―갈락토오스를 대사하는 재조합 미생물 및 이의 용도 - Google Patents
3,6―안하이드로―l―갈락토오스를 대사하는 재조합 미생물 및 이의 용도 Download PDFInfo
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Abstract
본 발명은 3,6-안하이드로-L-갈락토오스를 대사하는 재조합 미생물 및 이의 용도에 관한 것으로, 보다 상세하게는 3,6-AHG의 대사 경로에 관여하는 효소 군을 발현하는 재조합 미생물로부터 에탄올을 제조할 수 있다.
Description
본 발명은 비발효성당인 3,6-안하이드로-L-갈락토오스를 대사하는 재조합 미생물과 이의 용도에 관한 것이다.
석유자원의 고갈에 따른 에너지 안보 위기에 따라 전 세계적으로 화석연료를 대체하는 에너지 자원을 개발하기 위한 노력이 이루어지고 있다. 이러한 노력의 일환으로 화석원료를 바이오매스로 대체하여 지속 가능한 탄소경제로 전환하고 기존의 화학공정을 친환경적인 바이오공정으로 대체하여 바이오연료 및 바이오화학소재를 개발하는 연구가 이루어지고 있다. 이는 전후방산업의 패러다임을 전환할 수 있는 새로운 산업 군으로 온실가스 및 폐기물 발생을 저감할 수 있다는 장점이 있다.
바이오연료를 생산하기 위한 바이오매스로는 옥수수와 사탕수수와 같은 1세대 당질계 바이오매스에서 목질계 유래의 2세대 바이오매스로 전환되었으며 최근에는 3세대인 해조류 유래 바이오매스가 각광을 받고 있다.
해조류 바이오매스 중에서 우뭇가사리와 같은 홍조류는 녹조류와 갈조류에 비해 탄수화물 함량이 많은 것으로 알려져 있으며, 홍조류를 구성하는 주요 다당체인 아가로오스는 3,6-안하이드로-L-갈락토오스와 D-갈락토오스의 중합체이다. 이 중에서 D-갈락토오스는 미생물이 쉽게 이용할 수 있는 발효성 단당으로서 화학적 또는 효소적 처리 방법을 사용하여 홍조류 바이오매스를 가수분해하여 생산한 D-갈락토오스를 미생물로 발효하여 바이오 에탄올을 생산하는 연구가 많이 진행되어왔다. 최근에는 아가로오스를 분해하는 미생물인 사카로파거스 데그라단스(Saccharophagus degradans) 2-40, 슈도알테로모나스 아틀란티카(Pseudoalteromonas atlantica) T6c에서 3,6-안하이드로-L-갈락토오스를 전환하는 효소를 규명하였다(PCT/KR2012/000607). 뿐만 아니라 비발효성 희귀당으로 알려진 3,6-안하이드로-L-갈락토오스를 탄소원으로 대사할 수 있는 미생물인 비브리오 속(Vibrio sp.) EJY3의 유전체 서열이 밝혀짐에 따라 이 균주가 갖고 있는 3,6-안하이드로-L-갈락토오스 대사 관련 유전자 및 유전자의 기능 또한 밝혀지고 있다.
본 발명자들은 3,6-안하이드로-L-갈락토오스의 제조방법과 이의 기능성에 대한 연구들을 보고한바 있다(Yun EJ, et al . Process Biochem . (2011) 46(1):88-93. Yun EJ, et al . Appl . Microbiol . Biotechnol. (2013) 97(7) 2961-70). 예컨대, 3,6-안하이드로-L-갈락토오스의 환원 말단은 쉽게 수화가 되는 특성이 있는데 이로 인하여 보습 기능성을 나타내었다. 또한 미백 및 항산화 기능성이 밝혀졌고, 뿐만 아니라 대장암 예방 효과를 가진 것으로 나타났다(Yun EJ, et al . Appl . Microbiol. Biotechnol . (2013) 97(7) 2961-70).
그러나 3,6-안하이드로-L-갈락토오스는 일반적으로 미생물이 이용하지 못하는 비발효성 단당으로 알려져 있어 홍조류 바이오매스의 약 60% 이상이 탄수화물로 구성되어 있음에도 바이오연료의 생산 수율이 낮은 주된 원인으로 작용한다.
Michel G et al. Appl. Microbiol. Biotechnol. (2006) 71(1):23-33
Roh H, et al. J. Bacteriol. (2012) 194(10):2773-2774
본 발명의 목적은 3,6-안하이드로-L-갈락토오스의 대사 경로에 관여하는 효소 군의 재조합 벡터, 상기 재조합 벡터로 형질전환된 재조합 미생물 및 상기 재조합 미생물로부터 에탄올을 제조하는 방법을 제공하는 것이다.
상기 목적을 달성하기 위하여, 본 발명은 3,6-안하이드로-L-갈락토오스 디하이드로게나제(3,6-anhydro-L-galactose dehydrogenase)를 코딩하는 유전자; 3,6-안하이드로갈락토닉산 시클로이성질화효소(3,6-anhydrogalactonic acid cycloisomerase)를 코딩하는 유전자; 2-케토-3-데옥시-갈락토닉산 인산화효소(2-keto-3-deoxy-galactonic acid kinase)를 코딩하는 유전자; 및 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제(2-keto-3-deoxy-phosphogalactonic acid aldolase)를 코딩하는 유전자를 포함하는 에탄올 제조용 재조합 벡터를 제공한다.
본 발명은 또한 3,6-안하이드로-L-갈락토오스 디하이드로게나제(3,6-anhydro-L-galactose dehydrogenase)를 코딩하는 유전자; 3,6-안하이드로갈락토닉산 시클로이성질화효소(3,6-anhydrogalactonic acid cycloisomerase)를 코딩하는 유전자; 2-케토-3-데옥시-갈락토닉산 인산화효소(2-keto-3-deoxy-galactonic acid kinase)를 코딩하는 유전자; 및 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제(2-keto-3-deoxy-phosphogalactonic acid aldolase)를 코딩하는 유전자로 형질전환된 에탄올 제조용 재조합 미생물을 제공한다.
본 발명은 또한 본 발명에 따른 재조합 미생물을 탄소원으로 갈락토오스 및 3,6-안하이드로-L-갈락토오스로 이루어진 군으로부터 선택된 하나 이상을 사용하여 발효시키는 단계를 포함하는 에탄올의 제조방법을 제공한다.
본 발명은 또한 본 발명에 따른 재조합 미생물의 배양액 또는 균주 추출액을 갈락토오스 및 3,6-안하이드로-L-갈락토오스로 이루어진 군으로부터 선택된 하나 이상의 기질과 반응시켜 피루브산을 제조하는 단계; 및 상기 피루브산을 알코올 발효시키는 단계를 포함하는 에탄올의 제조방법을 제공한다.
본 발명은 3,6-안하이드로-L-갈락토오스의 대사 경로에 관여하는 효소 군을 발현하는 재조합 미생물로부터 에탄올을 제조하는 방법을 제공하는 효과가 있다.
따라서, 홍조류 바이오매스를 이용한 고부가 가치의 물질을 생산할 때 생산 수율을 높일 수 있는 핵심 기술로 제공될 수 있다.
도 1은 본 발명의 3,6-안하이드로-L-갈락토오스 디하이드로게나제 또는 3,6-안하이드로갈락토닉산 시클로이성질화효소를 발현하는 재조합 미생물에서 분리 정제된 효소의 효소 반응산물에 대한 GC-TOF MS로 분석한 결과를 도시한 것으로, A는 기질로 사용한 3,6-안하이드로-L-갈락토오스의 피크, B는 3,6-안하이드로-L-갈락토오스 디하이드로게나제의 반응산물인 3,6-안하이드로갈락토닉산의 피크, C는 3,6-안하이드로갈락토닉산 시클로이성질화효소의 반응산물인 2-케토-3-데옥시-갈락토닉산의 피크를 나타낸다.
도 2는 본 발명의 3,6-안하이드로-L-갈락토오스 디하이드로게나제를 발현하는 재조합 미생물에서 분리 정제된 3,6-안하이드로-L-갈락토오스 디하이드로게나제의 효소 반응산물에 대한 2차원 NMR 분석 결과를 나타낸 것으로, A는 2차원 Heteronuclear single quantum coherence spectroscopy (HSQC) NMR 분석 결과이고, B는 2차원 Heteronuclear Multible Bond Correlation (HMBC) NMR 분석결과이다.
도 3은 본 발명의 3,6-안하이드로갈락토닉산 시클로이성질화효소를 발현하는 재조합 미생물에서 분리 정제된 3,6-안하이드로갈락토닉산 시클로이성질화효소의 효소 반응산물에 대한 GC-TOF MS 분석 및 2차원 NMR 분석 결과로, A는 2-케토-3-데옥시-글루콘산 표준물질의 GC-TOF MS의 매스 스펙트럼 분석 결과, B는 3,6-안하이드로갈락토닉산 시클로이성질화효소의 효소 반응산물의 1차원 수소 NMR 분석 결과, C는 3,6-안하이드로갈락토닉산 시클로이성질화효소의 효소 반응산물의 2차원 HMBC NMR 분석 결과, D는 3,6-안하이드로갈락토닉산 시클로이성질화효소의 효소 반응산물의 2차원 HMBC NMR의 분석 결과를 나타낸 것이다.
도 4는 탄소원으로 3,6-안하이드로-L-갈락토오스를 사용한 본 발명의 3,6-안하이드로-L-갈락토오스 디하이드로게나제 및 3,6-안하이드로갈락토닉산 시클로이성질화효소를 각각 또는 동시에 발현하는 재조합 미생물의 생장 실험 결과이다.
도 5는 탄소원으로 3,6-안하이드로-L-갈락토오스(a), 갈락토오스(b), 또는, 3,6-안하이드로-L-갈락토오스 및 갈락토오스를 함유한 아가로오스 가수분해물(c)을 사용한 본 발명의 3,6-안하이드로-L-갈락토오스 디하이드로게나제 및 3,6-안하이드로갈락토닉산 시클로이성질화효소를 각각 또는 동시에 발현하는 재조합 미생물의 호기 조건에서의 생장 실험 결과이다.
도 6은 GC-FID를 이용한 에탄올의 정량 분석 곡선을 나타낸 것이다.
도 7은 본 발명의 3,6-안하이드로-L-갈락토오스 디하이드로게나제 및 3,6-안하이드로갈락토닉산 시클로이성질화효소를 각각 또는 동시에 발현하는 재조합 미생물의 발효 조건에서 생장 실험 결과(a), 기질 소비량 측정 결과(b), 발효에 의해 생성된 에탄올의 정량 분석 결과(c)이다.
도 8은 본 발명의 3,6-안하이드로-L-갈락토오스 디하이드로게나제, 3,6-안하이드로갈락토닉산 시클로이성질화효소, 2-케토-3-데옥시-갈락토닉산 인산화효소 및 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제를 동시에 발현하는 재조합 미생물의 탄소원에 따른 생장 실험 결과이다.
도 9는 본 발명의 3,6-안하이드로-L-갈락토오스 디하이드로게나제, 3,6-안하이드로갈락토닉산 시클로이성질화효소, 2-케토-3-데옥시-갈락토닉산 인산화효소 및 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제를 동시에 발현하는 재조합 미생물의 발효 조건에서 생장 실험 결과이다.
도 10은 본 발명의 3,6-안하이드로-L-갈락토오스 디하이드로게나제, 3,6-안하이드로갈락토닉산 시클로이성질화효소, 2-케토-3-데옥시-갈락토닉산 인산화효소 및 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제를 동시에 발현하는 재조합 미생물의 발효에 의해 생성된 에탄올의 정량 분석 결과이다.
도 2는 본 발명의 3,6-안하이드로-L-갈락토오스 디하이드로게나제를 발현하는 재조합 미생물에서 분리 정제된 3,6-안하이드로-L-갈락토오스 디하이드로게나제의 효소 반응산물에 대한 2차원 NMR 분석 결과를 나타낸 것으로, A는 2차원 Heteronuclear single quantum coherence spectroscopy (HSQC) NMR 분석 결과이고, B는 2차원 Heteronuclear Multible Bond Correlation (HMBC) NMR 분석결과이다.
도 3은 본 발명의 3,6-안하이드로갈락토닉산 시클로이성질화효소를 발현하는 재조합 미생물에서 분리 정제된 3,6-안하이드로갈락토닉산 시클로이성질화효소의 효소 반응산물에 대한 GC-TOF MS 분석 및 2차원 NMR 분석 결과로, A는 2-케토-3-데옥시-글루콘산 표준물질의 GC-TOF MS의 매스 스펙트럼 분석 결과, B는 3,6-안하이드로갈락토닉산 시클로이성질화효소의 효소 반응산물의 1차원 수소 NMR 분석 결과, C는 3,6-안하이드로갈락토닉산 시클로이성질화효소의 효소 반응산물의 2차원 HMBC NMR 분석 결과, D는 3,6-안하이드로갈락토닉산 시클로이성질화효소의 효소 반응산물의 2차원 HMBC NMR의 분석 결과를 나타낸 것이다.
도 4는 탄소원으로 3,6-안하이드로-L-갈락토오스를 사용한 본 발명의 3,6-안하이드로-L-갈락토오스 디하이드로게나제 및 3,6-안하이드로갈락토닉산 시클로이성질화효소를 각각 또는 동시에 발현하는 재조합 미생물의 생장 실험 결과이다.
도 5는 탄소원으로 3,6-안하이드로-L-갈락토오스(a), 갈락토오스(b), 또는, 3,6-안하이드로-L-갈락토오스 및 갈락토오스를 함유한 아가로오스 가수분해물(c)을 사용한 본 발명의 3,6-안하이드로-L-갈락토오스 디하이드로게나제 및 3,6-안하이드로갈락토닉산 시클로이성질화효소를 각각 또는 동시에 발현하는 재조합 미생물의 호기 조건에서의 생장 실험 결과이다.
도 6은 GC-FID를 이용한 에탄올의 정량 분석 곡선을 나타낸 것이다.
도 7은 본 발명의 3,6-안하이드로-L-갈락토오스 디하이드로게나제 및 3,6-안하이드로갈락토닉산 시클로이성질화효소를 각각 또는 동시에 발현하는 재조합 미생물의 발효 조건에서 생장 실험 결과(a), 기질 소비량 측정 결과(b), 발효에 의해 생성된 에탄올의 정량 분석 결과(c)이다.
도 8은 본 발명의 3,6-안하이드로-L-갈락토오스 디하이드로게나제, 3,6-안하이드로갈락토닉산 시클로이성질화효소, 2-케토-3-데옥시-갈락토닉산 인산화효소 및 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제를 동시에 발현하는 재조합 미생물의 탄소원에 따른 생장 실험 결과이다.
도 9는 본 발명의 3,6-안하이드로-L-갈락토오스 디하이드로게나제, 3,6-안하이드로갈락토닉산 시클로이성질화효소, 2-케토-3-데옥시-갈락토닉산 인산화효소 및 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제를 동시에 발현하는 재조합 미생물의 발효 조건에서 생장 실험 결과이다.
도 10은 본 발명의 3,6-안하이드로-L-갈락토오스 디하이드로게나제, 3,6-안하이드로갈락토닉산 시클로이성질화효소, 2-케토-3-데옥시-갈락토닉산 인산화효소 및 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제를 동시에 발현하는 재조합 미생물의 발효에 의해 생성된 에탄올의 정량 분석 결과이다.
이하 본 발명의 구성을 구체적으로 설명한다.
본 발명은 3,6-안하이드로-L-갈락토오스 디하이드로게나제(3,6-anhydro-L-galactose dehydrogenase)를 코딩하는 유전자; 3,6-안하이드로갈락토닉산 시클로이성질화효소(3,6-anhydrogalactonic acid cycloisomerase)를 코딩하는 유전자; 2-케토-3-데옥시-갈락토닉산 인산화효소(2-keto-3-deoxy-galactonic acid kinase)를 코딩하는 유전자; 및 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제(2-keto-3-deoxy-phosphogalactonic acid aldolase)를 코딩하는 유전자를 포함하는 에탄올 제조용 재조합 벡터에 관한 것이다.
본 발명의 에탄올 제조용 재조합 벡터는 갈락토오스 및/또는 3,6-안하이드로-L-갈락토오스(이하, '3,6-AHG'라 함)를 기질로 하여 최종 산물로 에탄올을 제조할 수 있는 것을 특징으로 한다. 보다 구체적으로, 상기 재조합 벡터는 3,6-AHG를 대사하는 3,6-안하이드로-L-갈락토오스 데히드로게나제를 코딩하는 유전자, 상기 3,6-안하이드로-L-갈락토오스 데히드로게나제에 의해 생산되는 3,6-안하이드로갈락토닉산의 환 구조를 개환시키면서 이성질화하여 2-케토-3-데옥시-갈락토닉산으로 전환하는 3,6-안하이드로갈락토닉산 시클로이성질화효소, 상기 2-케토-3-데옥시-갈락토닉산을 2-케토-3-데옥시-포스포갈락토닉산으로 인산화시키는 2-케토-3-데옥시-갈락토닉산 인산화효소, 및 상기 2-케토-3-데옥시-포스포갈락토닉산을 피루브산으로 분해시키는 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제를 코딩하는 유전자군을 포함하고 있다. 상기 피루브산은 알코올 발효의 출발물질로 이용되어 발효를 거쳐 최종적으로 에탄올을 생성하는 것이다.
상기 3,6-안하이드로-L-갈락토오스 디하이드로게나제는 3,6-AHG를 3,6-안하이드로갈락토닉산으로 전환하는 효소로, 비브리오 속(Vibrio sp.) EJY3, 사카로파거스 데그라단스(Saccharophagus degradans) 2-40, 또는 슈도알테로모나스 아틀란티카(Pseudoalteromonas atlantica ) T6c 등의 유래인 것일 수 있고, 예를 들어, 비브리오 속(Vibrio sp.) EJY3 유래의 SEQ ID NO: 1의 염기서열 및 SEQ ID NO: 2의 아미노산 서열로 표시될 수 있다.
상기 3,6-안하이드로갈락토닉산 시클로이성질화효소는 3,6-안하이드로갈락토닉산의 환 구조를 개환시키면서 이성질화하여 2-케토-3-데옥시-갈락토닉산으로 전환하는 효소로, 비브리오 속(Vibrio sp.) EJY3, 사카로파거스 데그라단스(Saccharophagus degradans) 2-40, 또는 슈도알테로모나스 아틀란티카(Pseudoalteromonas atlantica ) T6c 등의 유래인 것일 수 있고, 보다 구체적으로, 사카로파거스 데그라단스(Saccharophagus degradans) 2-40 유래의 SEQ ID NO: 3의 염기서열(아미노산 서열: SEQ ID NO: 4), 슈도알테로모나스 아틀란티카(Pseudoalteromonas atlantica ) T6c 유래의 SEQ ID NO: 5의 염기서열(아미노산 서열: SEQ ID NO: 6), 비브리오 속(Vibrio sp.) EJY3 유래의 SEQ ID NO: 7의 염기서열(아미노산 서열: SEQ ID NO: 8) 중 어느 하나로 표시될 수 있다.
본 발명자들은 AHG 대사효소 중 하나인 3,6-안하이드로-L-갈락토오스 디하이드로게나제와 클러스터를 이루는 유전자들을 유전공학 기법을 사용하여 각각의 단백질들의 획득하고 효소반응을 실시한 결과, 3,6-안하이드로갈락토닉산(이하 'AHGA'라 함)으로부터 화학양론의 변화없이 선형의 2-케토-3-데옥시-갈락토닉산을 생성하는 3,6-안하이드로 갈락토닉산 시클로이성질화효소를 최초로 동정하였다.
따라서, 본 발명은 SEQ ID NOS: 4, 6 또는 8의 아미노산 서열 중 어느 하나로 표시되는 3,6-안하이드로갈락토닉산 시클로이성질화효소(3,6-anhydrogalactonic acid cycloisomerase)을 포함하는 2-케토-3-데옥시-갈락토닉산 생산용 조성물을 또한 제공한다.
또한, 본 발명은 SEQ ID NOS: 4, 6 또는 8의 아미노산 서열 중 어느 하나로 표시되는 3,6-안하이드로갈락토닉산 시클로이성질화효소(3,6-anhydrogalactonic acid cycloisomerase), 상기 3,6-안하이드로갈락토닉산 시클로이성질화효소를 생산하는 미생물 또는 상기 미생물의 배양산물을 3,6-안하이드로갈락토닉산과 반응시켜 2-케토-3-데옥시-갈락토닉산을 생산하는 방법을 제공한다.
상기 2-케토-3-데옥시-갈락토닉산 인산화효소는 2-케토-3-데옥시-갈락토닉산을 2-케토-3-데옥시-포스포갈락토닉산으로 인산화시키는 효소로, 비브리오 속(Vibrio sp.) EJY3, 사카로파거스 데그라단스(Saccharophagus degradans) 2-40, 또는 슈도알테로모나스 아틀란티카(Pseudoalteromonas atlantica ) T6c 등의 유래인 것일 수 있고, SEQ ID NO: 9의 염기서열 및 SEQ ID NO: 10의 아미노산 서열로 표시될 수 있다.
상기 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제는 2-케토-3-데옥시-포스포갈락토닉산을 피루브산으로 분해시키는 효소로, 비브리오 속(Vibrio sp.) EJY3, 사카로파거스 데그라단스(Saccharophagus degradans) 2-40, 또는 슈도알테로모나스 아틀란티카(Pseudoalteromonas atlantica ) T6c 등의 유래인 것일 수 있고, SEQ ID NO: 11의 염기서열 및 SEQ ID NO: 12의 아미노산 서열로 표시될 수 있다.
상술한 유전자들은 효소의 물리 화학적 활성을 갖고 하나 이상의 아미노산이 결실, 치환, 삽입 및/또는 부가된 단백질을 코딩하는 폴리뉴클레오티드를 포함한다. 예컨대, SEQ ID NO: 1, 3, 5, 7, 9 또는 11에 기재된 어느 하나의 뉴클레오티드를 포함하고, 효소의 물리 화학적 특성을 갖는 단백질을 코딩하는 폴리뉴클레오티드에 엄격한 조건 하에서 혼성화하는 폴리뉴클레오티드도 포함한다. '엄격한 조건하에서 혼성화하는 폴리뉴클레오티드' 라 함은, 예컨대 설명서에 기술된 조건하(0.5×SSC를 포함하는 일차 세척 완충액으로 42℃에서 세척)에서 ECL 직접 핵산 표지화 및 검출 시스템(Amersham Pharmacia Biotech)을 이용하여, 효소 단백질로부터 임의적으로 선택된 적어도 20, 바람직하게는 적어도 30의 연속적 잔기(예를 들어, 40, 60 또는 100 연속 잔기)의 서열을 포함하는 하나 이상의 프로브 DNAs에 혼성화하는 폴리뉴클레오티드를 말한다. 본 발명의 폴리뉴클레오티드는 분리된 폴리뉴클레오티드를 포함한다. '분리된 뉴클레오티드'라 함은 천연적으로 발생하는 폴리뉴클레오티드에 비해 상이한 형태로 존재하는 폴리뉴클레오티드를 말한다. 예를 들어, 다른 생물체의 게놈에 통합된 벡터 및 폴리뉴클레오티드는 상기 분리된 폴리뉴클레오티드에 포함된다. 또한, 상기 분리된 폴리뉴클레오티드는 cDNA, PCR 산물, 또는 제한 단편으로서 얻어진 폴리뉴클레오티드를 포함한다. 또한, 융합 단백질을 코딩하는 폴리뉴클레오티드의 부분으로서 사용되는 폴리뉴클레오티드는 '분리된 폴리뉴클레오티드'에 또한 포함된다.
상술한 본 발명의 효소들을 코딩하는 폴리뉴클레오티드는 예를 들어, 하기 방법에 의해 분리할 수 있다: SEQ ID NO: 1, 3, 5, 7, 9 또는 11의 뉴클레오티드 서열에 기초한 각각의 PCR 프라이머를 설계하고, 주형(template)으로서 효소-생산 균주 유래의 염색체 DNA나 cDNA 라이브러리를 이용한 PCR을 수행하여 본 발명의 DNA를 얻는다.
또한, 본 발명의 폴리뉴클레오티드는 프로브로서 얻어진 DNA 단편을 이용하여, 콜로니 혼성화, 플라크 혼성화 등으로, (a) 효소-생산 균주에서 유래된 염색체 DNA의 제한효소 단편을 파지나 플라스미드에 도입하고 상기 파지나 벡터로 대장균 세포를 형질전환하여 얻어진 라이브러리, 또는 (b) cDNA 라이브러리에 대한 스크리닝을 수행함으로써 제조할 수 있다.
택일적으로, 본 발명의 폴리뉴클레오티드는 PCR로 얻어진 DNA 단편의 뉴클레오티드 서열을 분석; 알려진 DNA 서열의 외부에 가닥(strand)을 신장하기 위해 분석된 서열에 기초한 PCR 프라이머의 설계; 및 적절한 제한효소로 효소-생산 균주의 염색체 DNA의 소화 및 주형으로서 상기 DNA를 이용하는 자가환화 반응(self-cyclizing reaction)에 의한 역-PCR을 수행함으로써 얻어질 수 있다(Genetics, 120, 621-623 (1988)). 또한, 본 발명의 폴리뉴클레오티드는 RACE 방법으로 얻어질 수 있다(Rapid Amplification of cDNA End, 'PCR Jikken Manual (Manual for PCR experiments)', 25-33, HBJ Publishing Bureau).
상기 방법으로 클로닝된 게놈 DNA 및 cDNA에 더하여, 본 발명의 폴리뉴클레오티드는 합성된 DNAs를 포함한다.
본 발명에서 "재조합 벡터"란 적당한 숙주세포에서 목적 단백질을 발현할 수 있는 벡터로서, 유전자 삽입물이 발현되도록 작동가능하게 연결된 필수적인 조절 요소를 포함하는 유전자 작제물을 말한다. 상기 벡터는 플라스미드 벡터, 코즈미드 벡터, 박테리오파아지 벡터 또는 바이러스 벡터 등을 포함하나 이에 제한되지 않는다. 적합한 발현벡터는 프로모터, 오퍼레이터, 개시코돈, 종결코돈, 폴리아데닐화 시그널 및 인핸서 같은 발현 조절 엘리먼트 외에도 막 표적화 또는 분비를 위한 시그널 서열 또는 리더 서열을 포함하며, 목적에 따라 다양하게 제조될 수 있다. 벡터의 프로모터는 구성적 또는 유도성일 수 있다. 또한, 발현벡터는 벡터를 함유하는 숙주세포를 선택하기 위한 선택마커를 포함하고, 복제가능한 발현벡터인 경우 복제 기원을 포함한다.
본 발명의 재조합 벡터는 바람직하게는 일반적인 대장균 균주 발현용 벡터에 상술한 효소 코딩 핵산을 각각 또는 함께 삽입함으로써 제조될 수 있다. 상기 대장균 균주 발현용 벡터는 일반적으로 사용할 수 있는 모든 대장균주 발현용 벡터가 제한 없이 사용될 수 있다.
본 발명은 또한 3,6-안하이드로-L-갈락토오스 디하이드로게나제(3,6-anhydro-L-galactose dehydrogenase)를 코딩하는 유전자; 3,6-안하이드로갈락토닉산 시클로이성질화효소(3,6-anhydrogalactonic acid cycloisomerase)를 코딩하는 유전자; 2-케토-3-데옥시-갈락토닉산 인산화효소(2-keto-3-deoxy-galactonic acid kinase)를 코딩하는 유전자; 및 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제(2-keto-3-deoxy-phosphogalactonic acid aldolase)를 코딩하는 유전자로 형질전환된 에탄올 제조용 재조합 미생물에 관한 것이다.
상기 형질전환은 핵산을 유기체, 세포, 조직 또는 기관에 도입하는 어떤 방법도 포함되며, 당 분야에서 공지된 바와 같이 숙주세포에 따라 적합한 표준 기술을 선택하여 수행할 수 있다. 이런 방법에는 전기충격유전자전달법(electroporation), 원형질 융합, 인산칼슘(CaPO4) 침전, 염화칼슘(CaCl2) 침전, 실리콘 카바이드 섬유 이용한 교반, 아그로박테리아 매개된 형질전환, PEG, 덱스트란 설페이트, 리포펙타민 등이 포함되나 이로 제한되지 않는다.
또한, 숙주세포에 따라서 단백질의 발현량과 수식 등이 다르게 나타나므로, 목적에 가장 적합한 숙주세포를 선택하여 사용하면 된다.
숙주세포로는 대장균(Escherichia coli), 바실러스 서브틸리스(Bacillus subtilis), 스트렙토마이세스(Streptomyces), 슈도모나스(Pseudomonas), 프로테우스 미라빌리스(Proteus mirabilis) 또는 스타필로코쿠스(Staphylococcus)와 같은 원핵생물이 있으나 이에 제한되는 것은 아니다. 또한, 진균(예를 들어, 아스퍼질러스(Aspergillus)), 효모(예를 들어, 피치아 파스토리스(Pichia pastoris), 사카로마이세스 세르비시애(Saccharomyces cerevisiae), 쉬조사카로마세스(Schizosaccharomyces), 뉴로스포라 크라사(Neurospora crassa))등의 진핵생물이 사용될 수 있으나, 이에 제한하는 것은 아니다. 상기 형질전환체는 상기 유전자들을 포함하는 재조합 벡터를 임의의 숙주세포에 도입시킴으로써 용이하게 제조될 수 있다.
보다 구체적으로, 3,6-안하이드로-L-갈락토오스 디하이드로게나제를 코딩하는 유전자를 포함하는 재조합 벡터; 3,6-안하이드로갈락토닉산 시클로이성질화효소를 코딩하는 유전자를 포함하는 재조합 벡터; 2-케토-3-데옥시-갈락토닉산 인산화효소를 코딩하는 유전자를 포함하는 재조합 벡터; 및 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제를 코딩하는 유전자를 포함하는 재조합 벡터로 형질전환될 수 있다.
또는, 3,6-안하이드로-L-갈락토오스 디하이드로게나제를 코딩하는 유전자 및 3,6-안하이드로갈락토닉산 시클로이성질화효소를 코딩하는 유전자를 포함하는 재조합 벡터; 2-케토-3-데옥시-갈락토닉산 인산화효소를 코딩하는 유전자를 포함하는 재조합 벡터; 및 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제를 코딩하는 유전자를 포함하는 재조합 벡터로 형질전환될 수 있다.
또는, 3,6-안하이드로-L-갈락토오스 디하이드로게나제를 코딩하는 유전자, 3,6-안하이드로갈락토닉산 시클로이성질화효소를 코딩하는 유전자, 2-케토-3-데옥시-갈락토닉산 인산화효소를 코딩하는 유전자 및 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제를 코딩하는 유전자를 포함하는 재조합 벡터로 형질전환될 수 있다.
본 발명에 따른 재조합 미생물은 발효 균주일 수 있다.
본 발명은 또한 본 발명에 따른 재조합 미생물을 탄소원으로 갈락토오스 및 3,6-안하이드로-L-갈락토오스로 이루어진 군으로부터 선택된 하나 이상을 사용하여 발효시키는 단계를 포함하는 에탄올의 제조방법에 관한 것이다.
본 발명에 따른 재조합 미생물은 알코올 발효의 출발물질인 피루브산을 생산할 수 있어 3,6-AHG를 대사할 수 있는 효소들로부터 탄소원으로 갈락토오스 및/또는 3,6-AHG를 사용하여 발효 조건에서 에탄올을 생성할 수 있다.
상기 발효 시 유도물질로 아라비노스를 사용할 수 있다.
본 발명은 또한 본 발명에 따른 재조합 미생물의 배양액 또는 균주 추출액을 갈락토오스 및 3,6-안하이드로-L-갈락토오스로 이루어진 군으로부터 선택된 하나 이상의 기질과 반응시켜 피루브산을 제조하는 단계; 및 상기 피루브산을 알코올 발효시키는 단계를 포함하는 에탄올의 제조방법에 관한 것이다.
본 발명에 따른 재조합 미생물은 3,6-AHG를 대사할 수 있는 효소 군을 발현할 수 있고, 상기 재조합 미생물의 배양액 또는 균주 추출액에는 이러한 효소 군이 포함되어 있어 갈락토오스 및/또는 3,6-AHG를 기질로 제공하여 반응시킬 경우 피루브산을 생산할 수 있다. 상기 피루브산은 알코올 발효의 출발물질로 발효 조건에서 에탄올을 생산할 수 있다.
이하, 본 발명을 실시예를 통해 상세히 설명한다. 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명의 범위가 하기 실시예에 한정되는 것은 아니다.
<실시예 1> 3,6-안하이드로-L-갈락토오스 디하이드로게나제 재조합 미생물의 제조
비브리오 속(Vibrio sp.) EJY3 유래 3,6-안하이드로-L-갈락토오스 디하이드로게나제를 클로닝하였다. 이를 위해, 3,6-안하이드로-L-갈락토오스 디하이드로게나제 코딩 유전자(ORF Names: VEJY3_09240)에 대한 염기서열 정보를 기반으로 다음과 같은 프라이머 세트를 제작하였다.
정방향 프라이머 1: 5'-gaaggagatataaggatgaaacgttaccaaatgtacgttg-3'(SEQ ID NO: 13)
역방향 프라이머 2: 5'-atgatggtgatggtggtcgaaattcacatagaatgtcttc-3'(SEQ ID NO: 14)
중합효소연쇄반응을 통해 증폭된 각각의 효소 유전자는 pBAD (Invitrogen, Product no. V440-01 벡터와 아미노 말단에 6개의 히스티딘 잔기가 부가된 변형된 pET21α (이하 pJL) 벡터에 클로닝한 다음 발현용 대장균인 대장균(E. coli) BL21 (DB3)에 형질전환하여 발현시켰다. 이때 사용한 중합효소연쇄반응 조건은 다음과 같다. 1) 초기 변성 조건(Initial denaturation): 97℃, 30초, 2) 어닐링 조건: 35 사이클: 97℃, 10초 - 57℃, 1분 - 72℃, 2분, 3) 최종 연장 조건(final extension): 72℃, 5분.
pBAD 벡터에 클로닝한 3,6-안하이드로-L-갈락토오스 디하이드로게나제는 유도제로 0.2%(w/v) 아라비노스를 이용하여 16℃, 200rpm 조건에서 18시간 동안 발현을 유도하였다. 대장균(E. coli) BL21에서 과발현 시킨 효소는 His-trap 컬럼을 사용하여 정제하였다.
상기 정제된 3,6-안하이드로-L-갈락토오스 디하이드로게나제 200㎍을 10mM의 3,6-AHG 및 1.5mM의 NADP 보조인자와 함께 20mM Tris-HCl(pH 7.4)에서 30℃에서 1시간 동안 반응시키고, 반응산물은 GC-TOF MS(gas chromatography-time of flight mass spectrometry)로 분석하고, 2차원 NMR(nuclear magnetic resonance) 분석을 통해 화학 구조를 규명하였다.
상기 GC-TOF MS 분석을 위해 건조시킨 효소 반응산물에 유도체화 반응을 실시하였다. 40mg/mL의 메톡시아민 하이드로클로라이드(methoxyamine hydrochloride)를 피리딘(Sigma-Aldrich, St. Louis, MO)에 녹인 용액에 5㎕ 넣어준 후 30℃에서 90분간 반응시켰다. 그 후 45㎕의 N-메틸-N-트리메틸실릴트리플루오로아세타마이드(N-methyl-N-trimethylsilyltrifluoroacetamide, Fluka, Buchs, Switzerland)를 넣고 37℃에서 30분간 반응시켰다. 유도체화 시킨 샘플은 Agilent 7890 A GC(Agilent Technologies, Wilmington, DE) coupled to a Pegasus HT TOF MS(LECO, St. Joseph, MI)를 사용하여 분석하였다. RTX-5Sil MS 컬럼(30m×0.25mm, 0.25-㎛ film thickness; Restek, Bellefonte, PA)을 사용하였으며 1㎕의 샘플을 비분할 모드(splitless mode)로 주입(injection)하였다. 오븐 온도는 처음에 50℃에서 1분간 머무름 시간을 주었고, 그 후에 20℃/min의 속도로 330℃까지 승온시킨 후 5분간 머무름 시간을 주었다. 이온 소스(Ion source) 온도는 250℃였고, 트랜스퍼 라인(transfer line)의 온도는 280℃였다. 매스 스펙트럼(Mass spectra)의 스캔 범위는 85-500 m/z였다.
반응산물은 Sephadex G-10 컬럼을 사용하여 정제하였다. 즉, 2mg의 각각의 정제된 반응산물은 Bruker Avance II 900 MHz NMR spectrometer를 사용하여 13C NMR, 1H-13C HSQC NMR 및 1H-13C HMBC NMR 분석을 통해 화학구조를 규명하였으며 이때 사용한 내부 표준물질(internal standard)은 3-(트리메틸실릴)-프로피오닉-2,2,3,3,-d4애시드(3-(trimethylsilyl)-propionic-2,2,3,3-d4acid)로 하였다.
도 1A는 기질로 사용한 3,6-AHG이며, 도 1B는 3,6-안하이드로-L-갈락토오스 디하이드로게나아제와의 효소 반응 결과 반응산물로 3,6-안하이드로갈락토닉산이 생성됨을 나타낸 것이다.
도 2는 3,6-안하이드로-L-갈락토오스 디하이드로게나제의 반응산물의 NMR 분석 결과로, 1번 탄소와 1번 수소의 상관 스팟이 나타나지 않아 3,6-AHG의 알데히드기가 3,6-안하이드로-L-갈락토오스 디하이드로게나제의 효소 반응에 의해 전환되었음을 알 수 있었고(도 2A), 3번 탄소와 6번 수소간의 상관(correlation)이 나타나는 것으로 보아 3,6-안하이드로 결합은 그대로 유지가 된 채로 1번 탄소의 스팟이 180 PPM 부근에서 나타났으므로, 3,6-AHG의 알데히드기가 카르복실기로 산화된 것을 볼 수 있었다(도 2B).
따라서 3,6-안하이드로-L-갈락토오스 디하이드로게나제의 효소 반응 산물은 3,6-안하이드로갈락토닉산임을 알 수 있다.
<실시예 2> 3,6-안하이드로갈락토닉산 시클로이성질화효소 재조합 미생물의 제조
사카로파거스 데그라단스(Saccharophagus degradans) 2-40, 슈도알테로모나스 아틀란티카(Pseudoalteromonas atlantica ) T6c, 비브리오속(Vibrio) EJY3 유래의 3,6-안하이드로-L-갈락토오스 디하이드로게나제를 클로닝하였다. 이를 위해, 사카로파거스 데그라단스(Saccharophagus degradans) 2-40, 슈도알테로모나스 아틀란티카(Pseudoalteromonas atlantica ) T6c, 비브리오속(Vibrio) EJY3 유전체 서열로부터 얻어진 ACI 유전자 서열(유럽분자생물학연구소 (EMBL) 염기서열데이터베이스 식별번호: 각각 CP000282, 1152nt와 CP000388, 1137nt 그리고 CP003241, 1089nt)에 대한 정보를 기반으로 다음과 같은 프라이머 세트를 제작하였다.
1) Sde
정방향 프라이머 1: 5'- gaaggagatataaggatgaaaattcataacatgaaaaattttatcaa-3' (47mer: SEQ ID NO: 15)
역방향 프라이머 2: 5'- atgatggtgatggtgtcattcagcaaaatacactgtcttc -3' (40mer: SEQ ID NO: 16)
2) Patl
정방향 프라이머 1: 5'- gaaggagatataaggatgatgagtgtcattaccaaactagaca-3' (43mer: SEQ ID NO: 17)
역방향 프라이머 2: 5'- atgatggtgatggtgagaatgtttaactaaatagggaagaag-3' (42mer: SEQ ID NO: 18)
3) Vejy3
정방향 프라이머 1: 5'- gaaggagatataaggatgaaaacaacaatcaaagacatcaaaa-3' (43mer: SEQ ID NO: 19)
역방향 프라이머 2: 5'- atgatggtgatggtgcacttcgtactgagcaattttgt-3' (38mer: SEQ ID NO: 20)
각각 해당하는 유전체 DNA을 주형으로 PCR을 통해 각각의 유전자를 증폭하였다. 증폭된 sdeACI, patlACI, vejy3ACI DNA의 N-말단 부분은 모두 정제를 위해 6개의 히스티딘 잔기를 암호화하는 유전자 서열을 포함한 변형된 pET21a (이하 pJL)벡터에 LIC (Ligation Independent Cloning) 방법을 사용하여 클로닝한 후, 발현용 대장균인 E. coli BL21(DE3) 균주에 형질전환하였다. 이때 사용한 중합효소연쇄반응 조건은 다음과 같다. 1) 초기 변성 조건(Initial denaturation): 97℃, 30초, 2) 어닐링 조건: 35 사이클: 97℃, 10초 - 57℃, 1분 - 72℃, 2분, 3) 최종 연장 조건(final extension): 72℃, 5분.
sdeACI, patlACI, vejy3ACI 각각의 유전자가 포함된 재조합 플라스미드를 E. coli BL21 (DE3)에 형질전환한 대장균을 50mg/L의 엠피실린 항생제가 들어있는 Luria-bertani 배지에 접종하고 37℃에서 OD600=0.5~1.0될 때까지 진탕배양하였다. 그 후에 0.5mM/L의 농도로 isopropyl-β-D-thiogalactopranoside(IPTG)를 사용하여 16℃에서 24시간 동안 발현을 유도하였다. 배양액을 4000rpm에서 15분 동안 원심분리하여 20mM Tris-HCl, pH 8.0 완충용액에 현탁한 균체를 초음파 파쇄기를 사용하여 균체로부터 조추출액을 만들었다. 조추출액은 4℃에서 15000rpm으로 40~60분 동안 원심분리하여 조효소액과 침전물로 분리하였다. 조효소액은 0.45㎛ 여과지로 여과한 후, 단계적으로 친화성 크로마토그래피, 이온 교환 크로마토그래피, 그리고 겔 여과 크로마토그래피를 사용하여 단백질을 정제하였다.
10% SDS-PAGE 분석 결과, 대략 42 kDa 크기의 효소를 얻을 수 있다(미도시됨).
정제한 3,6-안하이드로갈락토닉산 시클로이성질화효소(vejy3ACI) 25㎍을 상기 실시예 1에서 얻은 반응산물과 30℃에서 1시간 동안 반응시켰다. 반응산물은 GC-TOF MS로 분석하고, 2차원 NMR 분석을 통해 화학 구조를 규명하였으며, Sephadex G-10 컬럼을 사용하여 정제를 하였다. 분석 및 정제방법은 상기 실시예 1과 동일하게 실시하였다. 표준물질로, 2-케토-3-데옥시-글루콘산(Sigma, Product no. 12271)을 사용하였다.
도 1C에 나타난 바와 같이, 반응산물이 2-케토-3-데옥시-갈락토닉산임을 확인하였다.
도 3은 3,6-안하이드로갈락토닉산 시클로이성질화효소(vejy3ACI)의 반응산물의 NMR 분석 결과로, 2-케토-3-데옥시-글루콘산(2-keto-3-deoxy-gluconic acid) 표준물질의 매스 스펙트럼과 도 1C의 3,6-안하이드로갈락토닉산 시클로이성질화효소의 효소 반응산물의 매스 스펙트럼이 일치하는 것으로 보아 3,6-안하이드로갈락토닉산 시클로이성질화효소의 효소 반응산물은 2-케토-3-데옥시-글루콘산과 같은 분자량과 2차원 구조를 갖고 있는 물질임을 알 수 있었다(도 3A). 또한, 1번 탄소의 카르복실기와 2번 탄소의 헤미케탈기(hemi-ketal structure)의 피크가 나타났고(도 3B), 1번 탄소와 6번 수소간의 상관 스팟(correlation spot)이 나타나지 않은 것으로 보아 1번 탄소의 카르복실기는 그대로 있음을 알 수 있다(도 3C). 또한 3번 탄소와 6번 탄소의 상관 스팟(correlation spot)이 나타나지 않은 것으로 보아 3,6-안하이드로 결합은 열린 것을 알 수 있으며, 2번 탄소와 6번 수소간의 상관 스팟이 나타났고(도 3D), 뿐만 아니라 3,6-안하이드로갈락토닉산에서 나타난 카르복실산(13C 180 PPM) 시그널이 그대로 남아 있으므로 1번 탄소의 카르복실산은 그대로 유지되어 3,6-안하이드로갈락토닉산 시클로이성질화효소의 효소 반응산물은 2-케토-3-데옥시-갈락토닉산임을 알 수 있었다.
<실시예 3> 3,6-안하이드로-L-갈락토오스 디하이드로게나제 및 3,6-안하이드로갈락토닉산 시클로이성질화효소의 재조합 미생물의 제조
재조합 대장균의 생장 실험을 위해 비브리오 속(Vibrio sp.) EJY3 유래 3,6-안하이드로-L-갈락토오스 디하이드로게나제 및 3,6-안하이드로갈락토닉산 시클로이성질화효소는 각각 또는 2개의 효소 코딩 유전자를 동시에 pBAD 벡터에 클로닝 하여 대장균(E. coli) K12 MG1655에 형질전환 시켰다. 이때 사용한 프라이머 정보는 다음과 같다:
1. 효소
각각을
클로닝한
경우
1.1. 3,6-안하이드로-L-갈락토오스 디하이드로게나제 코딩 유전자(ORF Names: VEJY3_09240)
정방향 프라이머 1: 5'-gaaggagatataaggatgaaacgttaccaaatgtacgttg-3'(SEQ ID NO: 13)
역방향 프라이머 2: 5'-atgatggtgatggtggtcgaaattcacatagaatgtcttc-3'(SEQ ID NO: 14)
1.2. 3,6-안하이드로갈락토닉산 시클로이성질화효소 코딩 유전자(ORF Names: VEJY3_09370)
정방향 프라이머 1: 5'-gcgctcgagatgaaaacaacaatcaaagacatcaaaac-3'(Tm:61.9, XhoI) (SEQ ID NO: 21)
역방향 프라이머 2: 5'-gcgtacgtacacttcgtactgagcaattttgtc-3'(Tm:61.8, SnabI) (SEQ ID NO: 22)
2. 효소를 동시에
클로닝한
경우: 3,6-
안하이드로
-L-갈락토오스
디하이드로게나제
코딩 유전자(
ORF
Names
:
VEJY3
_09240) 및 3,6-
안하이드로갈락토닉산
시클로
이성질화효소 코딩 유전자(
ORF
Names
:
VEJY3
_09370)
2.1. 3,6-안하이드로-L-갈락토오스 디하이드로게나제 코딩 유전자(VEJY3_09240)
정방향 프라이머 1: 5'-gcgctcgagatgaaacgttaccaaatgtacgttg-3'(XhoI) (SEQ ID NO: 23)
역방향 프라이머 2: 5'-gcgtctagattagtcgaaattcacatagaatgtct-3'(XbaI) (SEQ ID NO: 24)
2.2. 3,6-안하이드로갈락토닉산 시클로이성질화효소 코딩 유전자(VEJY3_09370)
정방향 프라이머 1: 5'-gcgtctagaatgaaaacaacaatcaaagacatcaaaac-3'(XbaI) (SEQ ID NO: 21)
역방향 프라이머 2: 5'-gcgtacgtacacttcgtactgagcaattttgtc-3'(SnabI) (SEQ ID NO: 22)
3,6-안하이드로-L-갈락토오스 디하이드로게나제 코딩 유전자(ORF Names: VEJY3_09240)와 3,6-안하이드로갈락토닉산 시클로이성질화효소 코딩 유전자(ORF Names: VEJY3_09370)를 동시에 pBAD에 클로닝 할 때에는 VEJY3_09240 프라이머 2의 XbaI 제한효소 자리와 VEJY3_09370 프라이머 1의 XbaI 제한효소자리가 라이게이션 반응 시 서로 연결되게 하였으며 연결된 VEJY3_09240와 VEJY3_09370 말단 자리의 XhoI와 SnabI 제한효소 자리가 pBAD 벡터와 연결되도록 하였다.
pBAD 벡터에 클로닝 하여 대장균(E. coli) K12 MG1655에 형질전환 시킨 각각의 효소들은 0.01%(w/v)의 아라비노스를 사용하여 발현시켰다. 각각의 효소 코딩 유전자가 들어있는 대장균(E. coli) K12 MG1655 균주는 변형한 M9 배지에서 배양하였다. M9 배지의 제조 방법은 다음과 같다. 5배 농축된 M9 염 용액을 만들기 위해 2.5g의 NaCl, 5g의 NH4Cl과 250mM의 Tris-HCl 완충용액(pH 7.4)를 1L의 물에 녹인 후에 멸균시켰다. 200mL의 5배 농축된 M9 염 용액에 2mL의 1M MgSO4, 0.1mL의 1M CaCl2, 20mL의 20%(w/v) 3,6-AHG와 20mL의 5%(w/v) YNB(yeast nitrogen base)를 넣은 후 멸균수로 총 부피가 1L가 되도록 첨가해 주었다. 재조합 대장균(E. coli) K12 MG1655 의 배양 조건은 30℃, 200rpm이었다.
탄소원으로 1%(w/v)의 3,6-AHG를 사용하고, 유도물질로 0.01%(w/v)의 아라비노스를 사용하여 상기 재조합 미생물을 배양한 결과, 도 4에 나타난 바와 같이, 유전자가 없는 빈 벡터만 있는 조건에서는 재조합 대장균(E. coli) K12 MG1655가 전혀 생장하지 않았으며 각각의 효소 3,6-안하이드로-L-갈락토오스 디하이드로게나제와 3,6-안하이드로갈락토닉산 시클로이성질화효소를 발현하는 재조합 대장균은 약간 생장하였으며 3,6-안하이드로-L-갈락토오스 디하이드로게나제 및 3,6-안하이드로갈락토닉산 시클로이성질화효소를 동시에 발현하는 재조합 대장균은 가장 높은 생장을 보였다.
상기 재조합 미생물을 호기적인 조건에서 M9 배지에서 30℃에서 96시간 동안 배양한 후, 600 nm에서 흡광도를 측정하였다. 이때, 탄소원으로 20mL의 20%(w/v) 3,6-AHG, 3,6-AHG와 갈락토오스가 주로 함유된 아가로스 가수분해물을 사용하였다. 이때, 탄소원으로 3,6-AHG, 3,6-AHG와 갈락토오스가 주로 함유된 아가로오스 가수분해물을 사용하였다.
그 결과, AHG 탄소원에서 재조합 대장균 배양 시, 3,6-안하이드로-L-갈락토오스 디하이드로게나제 유전자와 3,6-안하이드로갈락토닉산 시클로이성질화효소 유전자를 재조합한 조건에서만 생장하는 것을 확인하였다(도 5a). 또한 갈락토오스 조건에서는 빈 벡터(empty vector)와 2개의 효소유전자를 넣은 조건에서 비슷한 생장 곡선을 나타내었으며(도 5b), AHG와 갈락토오스가 주로 함유되어 있는 아가로스 가수분해물 탄소원 조건에서는 27시간까지는 비슷한 생장곡선을 나타내다가 그 이후로는 2개의 효소유전자를 넣은 조건에서 추가적인 생장을 나타내었다(도 5c).
또한, 상기 재조합 미생물을 미세호기조건(microaerobic)에서 에탄올 발효 실험을 진행하였다. 상기 재조합 미생물을 발효시켜 생성된 에탄올은 에탄올 표준물질 농도별로 GC-FID 분석을 실시하여 검정곡선을 나타내었다. 배양액을 원심분리 한 후(16,000rpm, 4℃, 5분), 상층액을 얻어 분석하였으며 분석 조건은 다음과 같았다. 주입구(Inlet)의 온도 250℃, split ration 20:1, 압력 11.567 psi, 전체 흐름 24mL/min, septum purge 흐름 3mL/min이었으며, 샘플 시료는 1㎕ 주입하였다. 오븐의 흐름은 1mL/min, 오븐 온도 조건은 처음에 40℃에서 3.5분간 머무른 후에 50℃/min의 속도로 150℃까지 승온 시킨 후 1분간 머무름 시간을 주었다. 그 후 20℃/min의 속도로 180℃까지 승온 시킨 후 2분간 머무름 시간을 주었으며 총 분석시간은 10.2분이었다. FID의 온도는 300℃였으며 수소 가스 흐름 40mL/min, 공기 흐름 350mL/min, 헬륨가스 흐름 15mL/min이었다. 도 6의 검정 곡선 결과 y=245.18x+12.24(y=피크 영역(peak area), x=에탄올 농도(ethanol concentration, g/L))의 수식을 얻을 수 있었으며 이를 바탕으로 에탄올 농도를 계산하였다.
미세호기조건에서의 세포밀도는 빈 벡터와 두 개의 효소유전자를 넣은 조건에서 모두 비슷하게 나타났으며(도 7a), 기질소비량을 측정한 결과, 갈락토오스의 소비량은 비슷하게 나타났지만, 갈락토오스를 모두 소비한 24시간 이후부터는 두 개의 효소유전자를 넣은 조건에서 AHG를 소비하는 것으로 나타났다(도 7b). 에탄올 생산은 두 개의 효소유전자를 넣은 조건에서 빈 벡터 조건보다 높게 나타났으며, 42시간에서는 빈 벡터 조건 대비 2개의 효소유전자를 넣은 조건에서 24% 높은 에탄올 농도를 나타내었다.
<실시예 4 > 3,6-AHG 대사 관련 효소 군의 재조합 미생물의 제조
3,6-AHG 대사에 관련된 효소, 즉, 3,6-안하이드로-L-갈락토오스 디하이드로게나제, 3,6-안하이드로갈락토닉산 시클로이성질화효소, 2-케토-3-데옥시-갈락토닉산 인산화효소 및 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제를 발효용 대장균(E. coli) KO11 FL 균주에 도입하였다. 이때 사용한 프라이머 정보는 다음과 같다:
1) 3,6-안하이드로-L-갈락토오스 디하이드로게나제 코딩 유전자(VEJY3_09240)
정방향 프라이머 1: 5'-gcgctcgagatgaaacgttaccaaatgtacgttg-3'(XhoI)(SEQ ID NO: 23)
역방향 프라이머 2: 5'-gcgtctagattagtcgaaattcacatagaatgtct-3'(XbaI)(SEQ ID NO: 24)
2) 2-케토-3-데옥시-갈락토닉산 인산화효소 코딩 유전자 + 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제 코딩 유전자 + 3,6-안하이드로갈락토닉산 시클로이성질화효소 코딩 유전자(각각 VEJY3_09380 + VEJY3_09375 + VEJY3_09370)
정방향 프라이머 1: 5'-gcgtctagaatgagtttggaaataaaacaagatacg-3'(XbaI)(SEQ ID NO: 21)
역방향 프라이머 2: 5'-gcgtacgta cacttcgtactgagcaattttgtc-3'(SnabI)(SEQ ID NO: 22)
3,6-안하이드로-L-갈락토오스 디하이드로게나제 코딩 유전자(ORF Names: VEJY3_09240)와 2-케토-3-데옥시-갈락토닉산 인산화효소 코딩 유전자 + 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제 코딩 유전자 + 3,6-안하이드로갈락토닉산 시클로이성질화효소 코딩 유전자(각각 VEJY3_09380 + VEJY3_09375 + VEJY3_09370)를 동시에 pBAD에 클로닝 할 때에는 VEJY3_09240 프라이머 2의 XbaI 제한효소 자리와 VEJY3_09380 + VEJY3_09375 + VEJY3_09370 프라이머 1의 XbaI 제한효소 자리가 라이게이션 반응 시에 서로 연결되게 하였으며 연결된 VEJY3_09240와 VEJY3_09380 + VEJY3_09375 + VEJY3_09370 말단 자리의 XhoI와 SnabI 제한효소 자리가 pBAD 벡터와 연결되도록 하였다. 재조합 대장균(E. coli) KO11 FL 균주의 효소 발현 및 배양 방법은 상기 실시예 1 및 2의 재조합 대장균(E. coli) K12 MG1655에서 사용한 방법과 동일하게 하였다. 이때 배지의 탄소원으로 1%의 갈락토오스 또는 1% 갈락토오스 + 1% 3,6-AHG를 사용하였다.
상기 재조합 미생물을 배양하여 생장 실험을 실시하였다. 배지 조성은 상술한 변형한 M9 배지를 사용하였으며, 탄소원으로 탄소원을 넣지 않은 조건(대조군), 유도물질 없이 1%(w/v)의 3,6-AHG만 넣은 조건, 유도물질인 0.01%(w/v)의 아라비노스만 있는 조건, 그리고 1%(w/v)의 3,6-AHG에 0.01%(w/v)의 아라비노스를 넣은 조건에서 배양하였다.
도 8에 나타난 바와 같이, 1%(w/v)의 3,6-AHG에 0.01%(w/v)의 아라비노스를 넣은 조건에서만 세포 밀도의 증가를 관찰하였다.
상기 재조합 미생물을 아가로오스 분해산물인 갈락토오스와 3,6-AHG 혼합당 조건에서 발효를 실시하였다. 이때 배지의 탄소원으로는 1%(w/v)의 갈락토오스와 혼합당 (1%(w/v)의 갈락토오스 + 1%(w/v)의 3,6-AHG) 조건에서 발효를 시행하였으며 0.01%(w/v)의 아라비노스를 유도물질로 사용하였다.
도 9에 나타난 바와 같이, 혼합당 조건에서 1%(w/v)의 갈락토오스만 넣어준 조건보다 세포밀도가 더 높게 나타났다.
상기 재조합 미생물을 미세호기조건에서 상기 실시예 3의 방법과 동일하게 알코올 발효 실험을 진행하였다.
도 10에 나타난 바와 같이, 혼합당 발효 시 4.11 g/L의 에탄올을 생산하였고, 갈락토오스 발효 시에는 1.93 g/L의 에탄올을 생산하였다.
<110> KOREA UNIVERSITY RESEARCH AND BUSINESS FOUNDATION
<120> Recombinant microorganisms metabolizing 3,6-anhydro-L-galactose
and use thereof
<130> P14U13C0477
<150> 2013-0051134
<151> 2013-05-07
<150> 2013-0069750
<151> 2013-06-18
<160> 24
<170> KopatentIn 2.0
<210> 1
<211> 1443
<212> DNA
<213> Vibrio sp. EJY3
<400> 1
atgaaacgtt accaaatgta cgttgacggc cagtggattg acgctgagaa cggcaaagtt 60
gatcaggtta ttaacccgtc aaccgaagaa gtgcttgctg agattcagga tggtgaccaa 120
gatgatgctg agcgcgtttt aagtgtggct aaacgtgcac aatctgactg gaaacgagtg 180
cccgcgcgtc aacgtgctga actgttgaga aagtttgctc aagaaatccg taataaccgt 240
gagcatcttg cagagttact cgtgagcgaa caaggcaaat tataccgagt tgcgttgggg 300
gaagtcgatg tagctgcatc ttttatcgaa tacgcctgtg actgggctcg tcagatggat 360
ggcgatattg ttcaatctga taatgtgaac gaacatatct ggattcaaaa aattcctcgt 420
ggtgtcgtgg tcgcgatcac tgcatggaat ttcccatttg cattagcagg tcgcaagata 480
ggaccagcac tggttgcggg taacactatt gttgttaaac caacctctga aactccgcta 540
gcaacgctag agttaggcta tattgctgaa aaagtaggta ttcctgcagg tgtactcaat 600
atagttaccg gtggtggagc aagcttaggt ggcgctttaa ctagtcaccg ttatacaaat 660
atggtcacta tgacaggttc aacacccgtt ggtcagcaga taatcaaagc atctgcgaat 720
aacatggctc acgttcaact agagctcggt ggtaaagcac cgttcatcgt aatggaagat 780
gctgatctgg agcaagctgc tgccgctgca ctacattcac gcttcgacaa ctgtggtcag 840
gtatgtacat gtaacgaacg tatgtatgtg cactctagtg tctacgatga attcatggcg 900
atctttatgg agaaagtcca aaatatcaaa gtgggtaatc ctatggatcc agaatctgat 960
atgggtccta aagtaaacaa acgagagctt gatcatatgg aagcattagt cgcgcaggca 1020
ttgaaagaag gcgcgcaact tttgcatggt ggcaagcgcc ttacggaggg tgagtttgga 1080
aagggcttct ggtttgaacc cacaatctta ggtaatgttc aacaatcaat gacgattgtt 1140
catgaagagg catttggtcc aattcttcct gttataaaat tcgacacttt tgaagaagtc 1200
attgattacg caaatgatag tgagtatggc ttggcaacta tgatttgtac gcgaaatatg 1260
aagtatgtac atcgcttaac tcacgagctt gaatgtggtg agatttatgt gaaccgtggt 1320
catggagaac agcatcaagg tttccataat ggatataaac tgagcggaac tggtggtgaa 1380
gatggaaaat atggcttcga acaatattta gagaagaaga cattctatgt gaatttcgac 1440
taa 1443
<210> 2
<211> 480
<212> PRT
<213> Vibrio sp. EJY3
<400> 2
Met Lys Arg Tyr Gln Met Tyr Val Asp Gly Gln Trp Ile Asp Ala Glu
1 5 10 15
Asn Gly Lys Val Asp Gln Val Ile Asn Pro Ser Thr Glu Glu Val Leu
20 25 30
Ala Glu Ile Gln Asp Gly Asp Gln Asp Asp Ala Glu Arg Val Leu Ser
35 40 45
Val Ala Lys Arg Ala Gln Ser Asp Trp Lys Arg Val Pro Ala Arg Gln
50 55 60
Arg Ala Glu Leu Leu Arg Lys Phe Ala Gln Glu Ile Arg Asn Asn Arg
65 70 75 80
Glu His Leu Ala Glu Leu Leu Val Ser Glu Gln Gly Lys Leu Tyr Arg
85 90 95
Val Ala Leu Gly Glu Val Asp Val Ala Ala Ser Phe Ile Glu Tyr Ala
100 105 110
Cys Asp Trp Ala Arg Gln Met Asp Gly Asp Ile Val Gln Ser Asp Asn
115 120 125
Val Asn Glu His Ile Trp Ile Gln Lys Ile Pro Arg Gly Val Val Val
130 135 140
Ala Ile Thr Ala Trp Asn Phe Pro Phe Ala Leu Ala Gly Arg Lys Ile
145 150 155 160
Gly Pro Ala Leu Val Ala Gly Asn Thr Ile Val Val Lys Pro Thr Ser
165 170 175
Glu Thr Pro Leu Ala Thr Leu Glu Leu Gly Tyr Ile Ala Glu Lys Val
180 185 190
Gly Ile Pro Ala Gly Val Leu Asn Ile Val Thr Gly Gly Gly Ala Ser
195 200 205
Leu Gly Gly Ala Leu Thr Ser His Arg Tyr Thr Asn Met Val Thr Met
210 215 220
Thr Gly Ser Thr Pro Val Gly Gln Gln Ile Ile Lys Ala Ser Ala Asn
225 230 235 240
Asn Met Ala His Val Gln Leu Glu Leu Gly Gly Lys Ala Pro Phe Ile
245 250 255
Val Met Glu Asp Ala Asp Leu Glu Gln Ala Ala Ala Ala Ala Leu His
260 265 270
Ser Arg Phe Asp Asn Cys Gly Gln Val Cys Thr Cys Asn Glu Arg Met
275 280 285
Tyr Val His Ser Ser Val Tyr Asp Glu Phe Met Ala Ile Phe Met Glu
290 295 300
Lys Val Gln Asn Ile Lys Val Gly Asn Pro Met Asp Pro Glu Ser Asp
305 310 315 320
Met Gly Pro Lys Val Asn Lys Arg Glu Leu Asp His Met Glu Ala Leu
325 330 335
Val Ala Gln Ala Leu Lys Glu Gly Ala Gln Leu Leu His Gly Gly Lys
340 345 350
Arg Leu Thr Glu Gly Glu Phe Gly Lys Gly Phe Trp Phe Glu Pro Thr
355 360 365
Ile Leu Gly Asn Val Gln Gln Ser Met Thr Ile Val His Glu Glu Ala
370 375 380
Phe Gly Pro Ile Leu Pro Val Ile Lys Phe Asp Thr Phe Glu Glu Val
385 390 395 400
Ile Asp Tyr Ala Asn Asp Ser Glu Tyr Gly Leu Ala Thr Met Ile Cys
405 410 415
Thr Arg Asn Met Lys Tyr Val His Arg Leu Thr His Glu Leu Glu Cys
420 425 430
Gly Glu Ile Tyr Val Asn Arg Gly His Gly Glu Gln His Gln Gly Phe
435 440 445
His Asn Gly Tyr Lys Leu Ser Gly Thr Gly Gly Glu Asp Gly Lys Tyr
450 455 460
Gly Phe Glu Gln Tyr Leu Glu Lys Lys Thr Phe Tyr Val Asn Phe Asp
465 470 475 480
<210> 3
<211> 1152
<212> DNA
<213> Saccharophagus degradans 2-40
<400> 3
atgagtaaat gcctgatgga aagtatagtg gaattagagt tgcctcaagg taacccaatt 60
aaaataaaat ccgtagcagt cgagcattac aaggttccgc tagctgaagt gttgtctgat 120
gcaaagcacg gggatcatac ctattttgag ctaatagtta gccgtatcac ttgccaaaat 180
ggtgtagaag gtgtgggtta tacctatacc ggtgggtccg gcggttcggc aatctattcg 240
ctattagtcg atgaaattaa gcctatgctt gttgggcggg acgccaccca aattctagcc 300
atatgggaag aaatttattg gcgcttacat tatgttgggc gcggtggttt agttagcttt 360
gctcagtcag cggttgatat tgcattgtgg gatattcgct gcaagttgtt ggggcaaccc 420
ctgtggaaag tggcgggcgg tttaagcaat aaaacacgct gctatgccgg cggtatagat 480
ttaaattttt cgcaagaaaa actattaagc aatatacaag gttatttaga cgcgggcttt 540
aatgctgtaa aaattaaagt tggcaaagat aatattaaag aagatattgc gcgtgtacgc 600
gcagtgcgag agttaattgg caaagatacc acatttatgg tggatgccaa ctactccatg 660
accaaagaaa aagccattcg ttttgctaac gccatagaag accaaaatat tacttggttt 720
gaagagccaa cattgccaga cgattaccaa ggctatgccg atatcgctca agcaatatca 780
atacccctag ctatgggtga aaacctacac actattcacg aatttaccta tgccgtgcaa 840
caagccaagc ttggtttttt gcagcccgat gcttctaata ttggtggtat tactggttgg 900
ttgaacgttg caagtttagc aaacgcacac aacttaccgg tgtgcagtca cggcatgcaa 960
gagttgcacg tttcacttat gtcgtctcag cccaatgcgg gttatttaga agttcactcc 1020
tttcctatcg accaatacac aacacaaccg ctagcaatgg aaaacggtta cgcactagca 1080
ccagatatag aaggcacggg tgttgtgttt gtcgatgaat tattacgtgg ccatttggct 1140
aaaaaatcct aa 1152
<210> 4
<211> 383
<212> PRT
<213> Saccharophagus degradans 2-40
<400> 4
Met Ser Lys Cys Leu Met Glu Ser Ile Val Glu Leu Glu Leu Pro Gln
1 5 10 15
Gly Asn Pro Ile Lys Ile Lys Ser Val Ala Val Glu His Tyr Lys Val
20 25 30
Pro Leu Ala Glu Val Leu Ser Asp Ala Lys His Gly Asp His Thr Tyr
35 40 45
Phe Glu Leu Ile Val Ser Arg Ile Thr Cys Gln Asn Gly Val Glu Gly
50 55 60
Val Gly Tyr Thr Tyr Thr Gly Gly Ser Gly Gly Ser Ala Ile Tyr Ser
65 70 75 80
Leu Leu Val Asp Glu Ile Lys Pro Met Leu Val Gly Arg Asp Ala Thr
85 90 95
Gln Ile Leu Ala Ile Trp Glu Glu Ile Tyr Trp Arg Leu His Tyr Val
100 105 110
Gly Arg Gly Gly Leu Val Ser Phe Ala Gln Ser Ala Val Asp Ile Ala
115 120 125
Leu Trp Asp Ile Arg Cys Lys Leu Leu Gly Gln Pro Leu Trp Lys Val
130 135 140
Ala Gly Gly Leu Ser Asn Lys Thr Arg Cys Tyr Ala Gly Gly Ile Asp
145 150 155 160
Leu Asn Phe Ser Gln Glu Lys Leu Leu Ser Asn Ile Gln Gly Tyr Leu
165 170 175
Asp Ala Gly Phe Asn Ala Val Lys Ile Lys Val Gly Lys Asp Asn Ile
180 185 190
Lys Glu Asp Ile Ala Arg Val Arg Ala Val Arg Glu Leu Ile Gly Lys
195 200 205
Asp Thr Thr Phe Met Val Asp Ala Asn Tyr Ser Met Thr Lys Glu Lys
210 215 220
Ala Ile Arg Phe Ala Asn Ala Ile Glu Asp Gln Asn Ile Thr Trp Phe
225 230 235 240
Glu Glu Pro Thr Leu Pro Asp Asp Tyr Gln Gly Tyr Ala Asp Ile Ala
245 250 255
Gln Ala Ile Ser Ile Pro Leu Ala Met Gly Glu Asn Leu His Thr Ile
260 265 270
His Glu Phe Thr Tyr Ala Val Gln Gln Ala Lys Leu Gly Phe Leu Gln
275 280 285
Pro Asp Ala Ser Asn Ile Gly Gly Ile Thr Gly Trp Leu Asn Val Ala
290 295 300
Ser Leu Ala Asn Ala His Asn Leu Pro Val Cys Ser His Gly Met Gln
305 310 315 320
Glu Leu His Val Ser Leu Met Ser Ser Gln Pro Asn Ala Gly Tyr Leu
325 330 335
Glu Val His Ser Phe Pro Ile Asp Gln Tyr Thr Thr Gln Pro Leu Ala
340 345 350
Met Glu Asn Gly Tyr Ala Leu Ala Pro Asp Ile Glu Gly Thr Gly Val
355 360 365
Val Phe Val Asp Glu Leu Leu Arg Gly His Leu Ala Lys Lys Ser
370 375 380
<210> 5
<211> 1137
<212> DNA
<213> Pseudoalteromonas atlantica T6c
<400> 5
atgagtgtca ttaccaaact agacacacct gccatgaaca gttcacaaat tcagtcagtc 60
aatgttgagt tattcaacgt gccccttgac gaagtgttga acgatgctaa gcacggcgat 120
catacccact ttgagctgat cctatgcacc attacttgta ccgatggtac tcaaggcgtg 180
ggttatacct acacaggtgg taaaggtgga cgcgctatat actcactgct taatgacgaa 240
ctaaagcctt tcttgatggg taaagatgct agctgcatca atcatttatg ggaagaaatg 300
caatatcact tgcactatgt tggtcgtggc ggtttagtca gtttcgccat atccgcagtc 360
gatatcgccc tgtgggacat tcattgcaag gttcttaatc aacccttgtg gaaagtagct 420
gggggctgca gtgaccgcgt aaactgttat gcaggaggca ttgaccttaa tttttccact 480
gaaaaattgc tcggcaatat ccaaggctac ttagactgcg gctttgaagc ggtcaaaata 540
aaagtgggca aagaagatta tcgtgaagac gtggcccgcg tggcggctgt gcgcaacctg 600
attggtcctg atgcgatatt tatggtggat gcaaattatt cacttacagt caataaagcc 660
attaagtttg ctcaggcgat agagcagtat gatatcacct ggtttgaaga accgaccatt 720
cctgatgatt ttgccggttt tgctcacatt gccagcaaaa tcaatattcc gttggccatg 780
ggcgaaaacc tgcacactat ttacgaattc aaccaagcga taagccaagc caaacttggg 840
ttcttacaac ctgatgcatc gaatattggc ggtatcactg gttggctaac ggttgcccag 900
atgggctacg cgaacaactt acctatttgc agtcatggca tgcacgaatt acatgtatct 960
cttatggcat ctcagccaaa tgcgggttac ttggaagtac actcgtttcc cattgaccga 1020
tataccactc accctctgaa acttgaaaat ggcaaagccg ttgcgcccag tacacccggt 1080
gtaggcgtcg agttcaagac agagttactt cttccctatt tagttaaaca ttcttag 1137
<210> 6
<211> 378
<212> PRT
<213> Pseudoalteromonas atlantica T6c
<400> 6
Met Ser Val Ile Thr Lys Leu Asp Thr Pro Ala Met Asn Ser Ser Gln
1 5 10 15
Ile Gln Ser Val Asn Val Glu Leu Phe Asn Val Pro Leu Asp Glu Val
20 25 30
Leu Asn Asp Ala Lys His Gly Asp His Thr His Phe Glu Leu Ile Leu
35 40 45
Cys Thr Ile Thr Cys Thr Asp Gly Thr Gln Gly Val Gly Tyr Thr Tyr
50 55 60
Thr Gly Gly Lys Gly Gly Arg Ala Ile Tyr Ser Leu Leu Asn Asp Glu
65 70 75 80
Leu Lys Pro Phe Leu Met Gly Lys Asp Ala Ser Cys Ile Asn His Leu
85 90 95
Trp Glu Glu Met Gln Tyr His Leu His Tyr Val Gly Arg Gly Gly Leu
100 105 110
Val Ser Phe Ala Ile Ser Ala Val Asp Ile Ala Leu Trp Asp Ile His
115 120 125
Cys Lys Val Leu Asn Gln Pro Leu Trp Lys Val Ala Gly Gly Cys Ser
130 135 140
Asp Arg Val Asn Cys Tyr Ala Gly Gly Ile Asp Leu Asn Phe Ser Thr
145 150 155 160
Glu Lys Leu Leu Gly Asn Ile Gln Gly Tyr Leu Asp Cys Gly Phe Glu
165 170 175
Ala Val Lys Ile Lys Val Gly Lys Glu Asp Tyr Arg Glu Asp Val Ala
180 185 190
Arg Val Ala Ala Val Arg Asn Leu Ile Gly Pro Asp Ala Ile Phe Met
195 200 205
Val Asp Ala Asn Tyr Ser Leu Thr Val Asn Lys Ala Ile Lys Phe Ala
210 215 220
Gln Ala Ile Glu Gln Tyr Asp Ile Thr Trp Phe Glu Glu Pro Thr Ile
225 230 235 240
Pro Asp Asp Phe Ala Gly Phe Ala His Ile Ala Ser Lys Ile Asn Ile
245 250 255
Pro Leu Ala Met Gly Glu Asn Leu His Thr Ile Tyr Glu Phe Asn Gln
260 265 270
Ala Ile Ser Gln Ala Lys Leu Gly Phe Leu Gln Pro Asp Ala Ser Asn
275 280 285
Ile Gly Gly Ile Thr Gly Trp Leu Thr Val Ala Gln Met Gly Tyr Ala
290 295 300
Asn Asn Leu Pro Ile Cys Ser His Gly Met His Glu Leu His Val Ser
305 310 315 320
Leu Met Ala Ser Gln Pro Asn Ala Gly Tyr Leu Glu Val His Ser Phe
325 330 335
Pro Ile Asp Arg Tyr Thr Thr His Pro Leu Lys Leu Glu Asn Gly Lys
340 345 350
Ala Val Ala Pro Ser Thr Pro Gly Val Gly Val Glu Phe Lys Thr Glu
355 360 365
Leu Leu Leu Pro Tyr Leu Val Lys His Ser
370 375
<210> 7
<211> 1089
<212> DNA
<213> Vibrio sp. EJY3
<400> 7
atgaaaacaa caatcaaaga catcaaaacg agactgttta agattccgtt aaaggaaatt 60
ttatctgatg caaaacatgg tgatcatgac cactttgagc tgatcactac aacggtcacg 120
ttagaagatg gttcgcaggg aaccggctat acttatactg gtggcaaagg cggttactcg 180
atcaaagcga tgctagagta tgatattcag cctgcgctaa tcggcaaaga cgcgacgcaa 240
attgaagaga tctatgactt tatggagtgg catattcact atgtcggtcg tggcggtatc 300
tctacatttg cgatgtctgc ggtagacatt gcgctttggg atctaaaagg taaacgagaa 360
ggcttgccgt tatggaaaat ggctggtgga aaaaacaata cctgtaaagc gtactgtggt 420
ggcattgacc ttcagtttcc acttgagaaa ttgctcaaca atatttgtgg ttatttagaa 480
agtggcttca atgccgttaa gatcaagatt ggtcgcgaaa atatgcaaga agatattgac 540
cgcattaagg cggttcgcga gctgattggg ccagatatca cctttatgat cgatgccaac 600
tattcgttga cagtagaaca agcgatcaaa ctgtcaaaag cggtagagca atatgacatc 660
acgtggtttg aagagccaac attgccagat gactacaaag gttttgctga gattgctgac 720
aatacagcga ttccgttggc catgggggaa aaccttcaca ccattcatga gtttggttat 780
gcaatggacc aagcaaagct tggctactgc caaccagatg cctcaaactg tggtggcatt 840
accggttggt tgaaagcggc ggacttgatt acagaacata atatcccagt gtgtactcac 900
ggtatgcaag agctacacgt aagtcttgtt tcagcgtttg atacaggttg gctagaggtg 960
cacagcttcc cgattgatga atacaccaag cgtcctttgg ttgtagaaaa cttccgcgct 1020
gtggcgtcca atgagccggg tatcggggtc gagttcgatt gggacaaaat tgctcagtac 1080
gaagtgtaa 1089
<210> 8
<211> 362
<212> PRT
<213> Vibrio sp. EJY3
<400> 8
Met Lys Thr Thr Ile Lys Asp Ile Lys Thr Arg Leu Phe Lys Ile Pro
1 5 10 15
Leu Lys Glu Ile Leu Ser Asp Ala Lys His Gly Asp His Asp His Phe
20 25 30
Glu Leu Ile Thr Thr Thr Val Thr Leu Glu Asp Gly Ser Gln Gly Thr
35 40 45
Gly Tyr Thr Tyr Thr Gly Gly Lys Gly Gly Tyr Ser Ile Lys Ala Met
50 55 60
Leu Glu Tyr Asp Ile Gln Pro Ala Leu Ile Gly Lys Asp Ala Thr Gln
65 70 75 80
Ile Glu Glu Ile Tyr Asp Phe Met Glu Trp His Ile His Tyr Val Gly
85 90 95
Arg Gly Gly Ile Ser Thr Phe Ala Met Ser Ala Val Asp Ile Ala Leu
100 105 110
Trp Asp Leu Lys Gly Lys Arg Glu Gly Leu Pro Leu Trp Lys Met Ala
115 120 125
Gly Gly Lys Asn Asn Thr Cys Lys Ala Tyr Cys Gly Gly Ile Asp Leu
130 135 140
Gln Phe Pro Leu Glu Lys Leu Leu Asn Asn Ile Cys Gly Tyr Leu Glu
145 150 155 160
Ser Gly Phe Asn Ala Val Lys Ile Lys Ile Gly Arg Glu Asn Met Gln
165 170 175
Glu Asp Ile Asp Arg Ile Lys Ala Val Arg Glu Leu Ile Gly Pro Asp
180 185 190
Ile Thr Phe Met Ile Asp Ala Asn Tyr Ser Leu Thr Val Glu Gln Ala
195 200 205
Ile Lys Leu Ser Lys Ala Val Glu Gln Tyr Asp Ile Thr Trp Phe Glu
210 215 220
Glu Pro Thr Leu Pro Asp Asp Tyr Lys Gly Phe Ala Glu Ile Ala Asp
225 230 235 240
Asn Thr Ala Ile Pro Leu Ala Met Gly Glu Asn Leu His Thr Ile His
245 250 255
Glu Phe Gly Tyr Ala Met Asp Gln Ala Lys Leu Gly Tyr Cys Gln Pro
260 265 270
Asp Ala Ser Asn Cys Gly Gly Ile Thr Gly Trp Leu Lys Ala Ala Asp
275 280 285
Leu Ile Thr Glu His Asn Ile Pro Val Cys Thr His Gly Met Gln Glu
290 295 300
Leu His Val Ser Leu Val Ser Ala Phe Asp Thr Gly Trp Leu Glu Val
305 310 315 320
His Ser Phe Pro Ile Asp Glu Tyr Thr Lys Arg Pro Leu Val Val Glu
325 330 335
Asn Phe Arg Ala Val Ala Ser Asn Glu Pro Gly Ile Gly Val Glu Phe
340 345 350
Asp Trp Asp Lys Ile Ala Gln Tyr Glu Val
355 360
<210> 9
<211> 966
<212> DNA
<213> Vibrio sp. EJY3
<400> 9
atgagtttgg aaataaaaca agatacggag tctagctata gcgatattct tagctttggt 60
gagccaatgt ttgagtttag ccaagttgga caagcaggtt caggccagcc tgatttcttg 120
agtggttttg gtggtgatgc ttcgaacttt gctatcgcag cagcaagaca aggcgcatca 180
gttggaatgt tgacacaact tggcgacgat gaattcggta agcgttttgt tgagctgtgg 240
gaacagcagg gtgttagcag ttcagctgtg tgtatactac caaataaagc aacgggcgtt 300
tattttatta cgcacgatga tgagggacac catttttctt tcttgcgtaa gaactctgcg 360
gccagtttaa tgacaccgca agacttacca tcagatgcga ttgccaatgc taagcttctt 420
catatcactg ctattactca ggcgattagt gattcaagtt gtgactcagt gtttgcagca 480
attgaaacag cgaaagcgca cggcactcaa gtgtcctatg acaccaactt gcgcttaaag 540
ctatggtcac tgcaacgcgc tcgcgccatc attaatgaaa ccgcgtcact agtcgatgtc 600
tgcttcccta gtattgacga agcacgcttg gtgactggcc ttgaacatgc tgacgatatc 660
atcgattttt acctaaaagc aggcgcgaaa gttgtcgtac ttaaacaggg tggtgacggt 720
gcgacagtgg ctaatgagca tattaggcat ttcatccttc cgcataaagt gacacctgtt 780
gatgcgaccg ctgctggtga ttcatttgca ggctcattct gtacgcatta tgtcaacgga 840
gagtctttag agcagtgtct tgcgtatgca aatgccaccg cgtctatcac gattactggt 900
tttggtgcag ttgccccttt accgacattt gagcaagtgc ttgagaaaat caacgaatct 960
aaatag 966
<210> 10
<211> 321
<212> PRT
<213> Vibrio sp. EJY3
<400> 10
Met Ser Leu Glu Ile Lys Gln Asp Thr Glu Ser Ser Tyr Ser Asp Ile
1 5 10 15
Leu Ser Phe Gly Glu Pro Met Phe Glu Phe Ser Gln Val Gly Gln Ala
20 25 30
Gly Ser Gly Gln Pro Asp Phe Leu Ser Gly Phe Gly Gly Asp Ala Ser
35 40 45
Asn Phe Ala Ile Ala Ala Ala Arg Gln Gly Ala Ser Val Gly Met Leu
50 55 60
Thr Gln Leu Gly Asp Asp Glu Phe Gly Lys Arg Phe Val Glu Leu Trp
65 70 75 80
Glu Gln Gln Gly Val Ser Ser Ser Ala Val Cys Ile Leu Pro Asn Lys
85 90 95
Ala Thr Gly Val Tyr Phe Ile Thr His Asp Asp Glu Gly His His Phe
100 105 110
Ser Phe Leu Arg Lys Asn Ser Ala Ala Ser Leu Met Thr Pro Gln Asp
115 120 125
Leu Pro Ser Asp Ala Ile Ala Asn Ala Lys Leu Leu His Ile Thr Ala
130 135 140
Ile Thr Gln Ala Ile Ser Asp Ser Ser Cys Asp Ser Val Phe Ala Ala
145 150 155 160
Ile Glu Thr Ala Lys Ala His Gly Thr Gln Val Ser Tyr Asp Thr Asn
165 170 175
Leu Arg Leu Lys Leu Trp Ser Leu Gln Arg Ala Arg Ala Ile Ile Asn
180 185 190
Glu Thr Ala Ser Leu Val Asp Val Cys Phe Pro Ser Ile Asp Glu Ala
195 200 205
Arg Leu Val Thr Gly Leu Glu His Ala Asp Asp Ile Ile Asp Phe Tyr
210 215 220
Leu Lys Ala Gly Ala Lys Val Val Val Leu Lys Gln Gly Gly Asp Gly
225 230 235 240
Ala Thr Val Ala Asn Glu His Ile Arg His Phe Ile Leu Pro His Lys
245 250 255
Val Thr Pro Val Asp Ala Thr Ala Ala Gly Asp Ser Phe Ala Gly Ser
260 265 270
Phe Cys Thr His Tyr Val Asn Gly Glu Ser Leu Glu Gln Cys Leu Ala
275 280 285
Tyr Ala Asn Ala Thr Ala Ser Ile Thr Ile Thr Gly Phe Gly Ala Val
290 295 300
Ala Pro Leu Pro Thr Phe Glu Gln Val Leu Glu Lys Ile Asn Glu Ser
305 310 315 320
Lys
<210> 11
<211> 621
<212> DNA
<213> Vibrio sp. EJY3
<400> 11
atggatctca atcaacgttt agctaagctc aaagttgtgc ctgtgattgc tgtagataat 60
gcgcaagata ttttgccttt aggtaaggcg ctggtagaga atggtttacc agtcgcagaa 120
attacctttc gctctgacgc ggcgactgaa gccattcgtt tacttcgtac tacttatcca 180
gacatcttga ttggtgcggg tacggtattg aacgaagctc aagtaattga ggcaaaagag 240
gcgggtgctg actttattgt ttctccaggc ttgaacccaa tcacagtaaa agcatgtcaa 300
aaacataaaa taaccatcgt ccctggtgta aacagcccat cgttggttga gcaagctctt 360
gagcttggtg ttgatactgt taaatttttc ccagcagaag cgtcgggcgg tctagcgatg 420
ttgaagtcgt tgcttggccc ttatcaacaa atcaaagtga tgcctacagg tggtatcaat 480
caaaacaaca ttcatgatta tctggctctt cctgctgtac ttgcttgtgg tggtacgtgg 540
atggtggata aatcactggt acataaaggt gcttgggatg aaattggccg attggtcaga 600
gaaattgtcg ccgcagtata g 621
<210> 12
<211> 206
<212> PRT
<213> Vibrio sp. EJY3
<400> 12
Met Asp Leu Asn Gln Arg Leu Ala Lys Leu Lys Val Val Pro Val Ile
1 5 10 15
Ala Val Asp Asn Ala Gln Asp Ile Leu Pro Leu Gly Lys Ala Leu Val
20 25 30
Glu Asn Gly Leu Pro Val Ala Glu Ile Thr Phe Arg Ser Asp Ala Ala
35 40 45
Thr Glu Ala Ile Arg Leu Leu Arg Thr Thr Tyr Pro Asp Ile Leu Ile
50 55 60
Gly Ala Gly Thr Val Leu Asn Glu Ala Gln Val Ile Glu Ala Lys Glu
65 70 75 80
Ala Gly Ala Asp Phe Ile Val Ser Pro Gly Leu Asn Pro Ile Thr Val
85 90 95
Lys Ala Cys Gln Lys His Lys Ile Thr Ile Val Pro Gly Val Asn Ser
100 105 110
Pro Ser Leu Val Glu Gln Ala Leu Glu Leu Gly Val Asp Thr Val Lys
115 120 125
Phe Phe Pro Ala Glu Ala Ser Gly Gly Leu Ala Met Leu Lys Ser Leu
130 135 140
Leu Gly Pro Tyr Gln Gln Ile Lys Val Met Pro Thr Gly Gly Ile Asn
145 150 155 160
Gln Asn Asn Ile His Asp Tyr Leu Ala Leu Pro Ala Val Leu Ala Cys
165 170 175
Gly Gly Thr Trp Met Val Asp Lys Ser Leu Val His Lys Gly Ala Trp
180 185 190
Asp Glu Ile Gly Arg Leu Val Arg Glu Ile Val Ala Ala Val
195 200 205
<210> 13
<211> 40
<212> DNA
<213> Artificial Sequence
<220>
<223> Forward primer 1 for 3,6-anhydro-L-galactose dehydrogenase
<400> 13
gaaggagata taaggatgaa acgttaccaa atgtacgttg 40
<210> 14
<211> 40
<212> DNA
<213> Artificial Sequence
<220>
<223> Reverse primer 2 for 3,6-anhydro-L-galactose dehydrogenase
<400> 14
atgatggtga tggtggtcga aattcacata gaatgtcttc 40
<210> 15
<211> 47
<212> DNA
<213> Artificial Sequence
<220>
<223> Forward primer 1 for SdeACI
<400> 15
gaaggagata taaggatgaa aattcataac atgaaaaatt ttatcaa 47
<210> 16
<211> 40
<212> DNA
<213> Artificial Sequence
<220>
<223> Reverse primer 2 for SdeACI
<400> 16
atgatggtga tggtgtcatt cagcaaaata cactgtcttc 40
<210> 17
<211> 43
<212> DNA
<213> Artificial Sequence
<220>
<223> Forward primer 1 for Pat1ACI
<400> 17
gaaggagata taaggatgat gagtgtcatt accaaactag aca 43
<210> 18
<211> 42
<212> DNA
<213> Artificial Sequence
<220>
<223> Reverse primer 2 for Pat1ACI
<400> 18
atgatggtga tggtgagaat gtttaactaa atagggaaga ag 42
<210> 19
<211> 43
<212> DNA
<213> Artificial Sequence
<220>
<223> Forward primer 1 for Vejy3ACI
<400> 19
gaaggagata taaggatgaa aacaacaatc aaagacatca aaa 43
<210> 20
<211> 38
<212> DNA
<213> Artificial Sequence
<220>
<223> Reverse primer 2 for Vejy3ACI
<400> 20
atgatggtga tggtgcactt cgtactgagc aattttgt 38
<210> 21
<211> 38
<212> DNA
<213> Artificial Sequence
<220>
<223> Forward primer 1 for Vejy3ACI
<400> 21
gcgctcgaga tgaaaacaac aatcaaagac atcaaaac 38
<210> 22
<211> 33
<212> DNA
<213> Artificial Sequence
<220>
<223> Reverse primer 2 for Vejy3ACI
<400> 22
gcgtacgtac acttcgtact gagcaatttt gtc 33
<210> 23
<211> 34
<212> DNA
<213> Artificial Sequence
<220>
<223> Forward primer 1 for 3,6-anhydro-L-galactose dehydrogenase
<400> 23
gcgctcgaga tgaaacgtta ccaaatgtac gttg 34
<210> 24
<211> 35
<212> DNA
<213> Artificial Sequence
<220>
<223> Reverse primer 2 for 3,6-anhydro-L-galactose dehydrogenase
<400> 24
gcgtctagat tagtcgaaat tcacatagaa tgtct 35
Claims (13)
- 3,6-안하이드로-L-갈락토오스 디하이드로게나제(3,6-anhydro-L-galactose dehydrogenase)를 코딩하는 유전자;
3,6-안하이드로갈락토닉산 시클로이성질화효소(3,6-anhydrogalactonic acid cycloisomerase)를 코딩하는 유전자;
2-케토-3-데옥시-갈락토닉산 인산화효소(2-keto-3-deoxy-galactonic acid kinase)를 코딩하는 유전자; 및
2-케토-3-데옥시-포스포갈락토닉산 알돌라아제(2-keto-3-deoxy-phosphogalactonic acid aldolase)를 코딩하는 유전자를 포함하는 에탄올 제조용 재조합 벡터.
- 제1항에 있어서,
3,6-안하이드로-L-갈락토오스 디하이드로게나제를 코딩하는 유전자는 SEQ ID NO: 1의 염기서열로 표시되는 에탄올 제조용 재조합 벡터.
- 제1항에 있어서,
3,6-안하이드로갈락토닉산 시클로이성질화효소를 코딩하는 유전자는 SEQ ID NOS: 3, 5 또는 7의 염기서열 중 어느 하나로 표시되는 에탄올 제조용 재조합 벡터.
- 제1항에 있어서,
2-케토-3-데옥시-갈락토닉산 인산화효소를 코딩하는 유전자는 SEQ ID NO: 9의 염기서열로 표시되는 에탄올 제조용 재조합 벡터.
- 제1항에 있어서,
2-케토-3-데옥시-포스포갈락토닉산 알돌라아제를 코딩하는 유전자는 SEQ ID NO: 11의 염기서열로 표시되는 에탄올 제조용 재조합 벡터.
- 3,6-안하이드로-L-갈락토오스 디하이드로게나제(3,6-anhydro-L-galactose dehydrogenase)를 코딩하는 유전자;
3,6-안하이드로갈락토닉산 시클로이성질화효소(3,6-anhydrogalactonic acid cycloisomerase)를 코딩하는 유전자;
2-케토-3-데옥시-갈락토닉산 인산화효소(2-keto-3-deoxy-galactonic acid kinase)를 코딩하는 유전자; 및
2-케토-3-데옥시-포스포갈락토닉산 알돌라아제(2-keto-3-deoxy-phosphogalactonic acid aldolase)를 코딩하는 유전자로 형질전환된 에탄올 제조용 재조합 미생물.
- 제6항에 있어서,
3,6-안하이드로-L-갈락토오스 디하이드로게나제를 코딩하는 유전자를 포함하는 재조합 벡터;
3,6-안하이드로갈락토닉산 시클로이성질화효소를 코딩하는 유전자를 포함하는 재조합 벡터;
2-케토-3-데옥시-갈락토닉산 인산화효소를 코딩하는 유전자를 포함하는 재조합 벡터; 및
2-케토-3-데옥시-포스포갈락토닉산 알돌라아제를 코딩하는 유전자를 포함하는 재조합 벡터로 형질전환된 에탄올 제조용 재조합 미생물.
- 제6항에 있어서,
3,6-안하이드로-L-갈락토오스 디하이드로게나제를 코딩하는 유전자 및 3,6-안하이드로갈락토닉산 시클로이성질화효소를 코딩하는 유전자를 포함하는 재조합 벡터;
2-케토-3-데옥시-갈락토닉산 인산화효소를 코딩하는 유전자를 포함하는 재조합 벡터; 및
2-케토-3-데옥시-포스포갈락토닉산 알돌라아제를 코딩하는 유전자를 포함하는 재조합 벡터로 형질전환된 에탄올 제조용 재조합 미생물.
- 제6항에 있어서,
3,6-안하이드로-L-갈락토오스 디하이드로게나제를 코딩하는 유전자, 3,6-안하이드로갈락토닉산 시클로이성질화효소를 코딩하는 유전자, 2-케토-3-데옥시-갈락토닉산 인산화효소를 코딩하는 유전자 및 2-케토-3-데옥시-포스포갈락토닉산 알돌라아제를 코딩하는 유전자를 포함하는 재조합 벡터로 형질전환된 에탄올 제조용 재조합 미생물.
- 제6항에 있어서,
재조합 미생물은 발효 균주인 에탄올 제조용 재조합 미생물.
- 제6항 내지 제10항 중 어느 한 항에 따른 재조합 미생물을 탄소원으로 갈락토오스 및 3,6-안하이드로-L-갈락토오스로 이루어진 군으로부터 선택된 하나 이상을 사용하여 발효시키는 단계를 포함하는 에탄올의 제조방법.
- 제11항에 있어서,
발효 시 유도물질로 아라비노스를 첨가하는 에탄올의 제조방법.
- 제6항 내지 제10항 중 어느 한 항에 따른 재조합 미생물의 배양액 또는 균주 추출액을 갈락토오스 및 3,6-안하이드로-L-갈락토오스로 이루어진 군으로부터 선택된 하나 이상의 기질과 반응시켜 피루브산을 제조하는 단계; 및
상기 피루브산을 알코올 발효시키는 단계를 포함하는 에탄올의 제조방법.
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US14/889,376 US9637761B2 (en) | 2013-05-07 | 2014-05-07 | Recombinant microorganism metabolizing 3,6-anhydride-L-galactose and a use thereof |
PCT/KR2014/004033 WO2014182054A1 (ko) | 2013-05-07 | 2014-05-07 | 3,6-안하이드로-l-갈락토오스를 대사하는 재조합 미생물 및 이의 용도 |
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KR20130069750 | 2013-06-18 |
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KR101316084B1 (ko) | 2011-01-24 | 2013-11-13 | 고려대학교 산학협력단 | 3,6-안하이드로-l-갈락토오스에 작용하는 신규한 3,6-안하이드로-l-갈락토오스 데히드로게나제와 이 효소를 이용한 3,6-안하이드로 갈락토닉산의 생산 |
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2014
- 2014-05-07 US US14/889,376 patent/US9637761B2/en active Active
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- 2014-05-07 WO PCT/KR2014/004033 patent/WO2014182054A1/ko active Application Filing
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EP2995684A1 (en) | 2016-03-16 |
WO2014182054A1 (ko) | 2014-11-13 |
US20160115504A1 (en) | 2016-04-28 |
KR20140133455A (ko) | 2014-11-19 |
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