KR20240002283A - 2’-푸코실락토오스 제조방법 - Google Patents
2’-푸코실락토오스 제조방법 Download PDFInfo
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- KR20240002283A KR20240002283A KR1020220079144A KR20220079144A KR20240002283A KR 20240002283 A KR20240002283 A KR 20240002283A KR 1020220079144 A KR1020220079144 A KR 1020220079144A KR 20220079144 A KR20220079144 A KR 20220079144A KR 20240002283 A KR20240002283 A KR 20240002283A
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Abstract
본 발명은 2’-푸코실락토오스를 제조하는 방법에 관한 것이다.
Description
본 발명은 2’-푸코실락토오스 제조방법에 관한 것이다.
인간모유올리고당 (Human Milk Oligosaccharides, HMOs)의 약 80%는 푸코실화되어 있는 푸코실올리고당 (Fucosyloligosaccharide)으로, 신생아의 장내 미생물총의 형성에 영향을 미치는 것으로 알려져 있다. 푸코실올리고당 중 2’-푸코실락토오스는 가장 높은 함량으로 존재하고, 다양한 생물학적 기능을 나타내는 것으로 알려져 있다. 미생물을 이용한 2’-푸코실락토오스의 생산방법은 값싼 원료를 이용하여 대량생산이 가능하기 때문에 생산성이 높으나, 2’-푸코실락토오스와 젖당의 분자량이 유사하여 분리가 어려워, 고순도의 2’-푸코실락토오스를 생산하기 어려운 문제점이 있다.
본 발명의 일 예는 락토오스를 포함하는 배지에서 알파-1,2-푸코오스 전이효소(alpha-1,2-fucosyltransferase)를 가지는 미생물을 배양하고, 락토오스 가수분해효소를 처리하여 고순도의 2’-푸코실락토오스를 제조하는 방법을 제공하기 위한 것이다.
본 발명의 일 예는 락토오스를 포함하는 배지에서 알파-1,2-푸코오스 전이효소(alpha-1,2-fucosyltransferase)를 가지는 미생물을 배양하고, 락토오스 가수분해효소를 처리하여 고순도의 2’-푸코실락토오스를 제조하는 방법에 관한 것이다.
상기 락토오스 가수분해효소를 처리하는 단계는, 상기 미생물을 포함하는 배양액에서 수행되거나, 또는 상기 미생물 균체가 제거된 배양액에서 수행되는 것일 수 있다.
상기 락토오스 가수분해효소를 처리하는 단계는, 락토오스 가수분해효소를 상기 미생물을 포함하는 배양액에 처리하거나, 또는 상기 미생물 균체가 제거된 배양액에 처리하는 것일 수 있다.
상기 락토오스 가수분해효소는 상기 미생물을 포함하는 배양액에 처리되며, 상기 배양액에 락토오스 가수분해효소를 처리하여 배양을 지속하는 것일 수 있다.
상기 2’-푸코실락토오스를 제조하는 방법은, 상기 미생물의 배양액에서 균체를 제거하여 상등액을 얻는 단계를 추가로 포함하는 것일 수 있다. 또한, 상기 상등액을 정제하여 2’-푸코실락토오스를 얻는 단계를 추가로 포함하는 것일 수 있다. 또한, 상기 상등액을 농축 또는 분무건조하여 2’-푸코실락토오스 분말을 얻는 단계를 추가로 포함하는 것일 수 있다.
상기 알파-1,2-푸코오스 전이효소를 가지는 미생물은 탄소원으로 포도당 및 갈락토오스로 이루어지는 군에서 선택된 1종 이상을 사용 가능한 것일 수 있다.
상기 알파-1,2-푸코오스 전이효소를 가지는 미생물은 하기 (1) 내지 (4)로 이루어지는 군에서 선택된 1종 이상의 특징을 가지는 것일 수 있다:
(1) LacZ 유전자가 결실됨,
(2) 푸코오스 합성 유전자를 발현함,
(3) 락토오스 막 수송 단백질을 발현함, 및
(4) 탄소원으로 포도당 및 갈락토오스로 이루어지는 군에서 선택된 1종 이상을 사용 가능함.
이하, 본 발명을 더욱 자세히 설명하고자 한다.
본 발명의 일 예는 락토오스를 포함하는 배지에서 알파-1,2-푸코오스 전이효소(alpha-1,2-fucosyltransferase)를 가지는 미생물을 배양하여, 락토오스로부터 2’-푸코실락토오스를 생산하는 단계; 및 락토오스 가수분해효소를 처리하는 단계를 포함하는, 2’-푸코실락토오스의 제조 방법에 관한 것이다.
상기 락토오스 가수분해효소를 처리하는 단계는, 상기 미생물을 포함하는 배양액에서 수행되거나, 또는 상기 미생물 균체가 제거된 배양액에서 수행되는 것일 수 있다.
상기 락토오스 가수분해효소를 처리하는 단계는, 락토오스 가수분해효소를 상기 미생물을 포함하는 배양액에 처리하거나, 또는 상기 미생물 균체가 제거된 배양액에 처리하는 것일 수 있다.
일 예로, 상기 락토오스 가수분해효소는 상기 미생물을 포함하는 배양액에 처리되며, 상기 배양액에 락토오스 가수분해효소를 처리하여 미생물의 배양을 지속하는 것일 수 있다.
상기 락토오스 가수분해효소는 배양액 내의 락토오스가 포도당 및 갈락토오스로 분해되며, 최종 산물에서 2’-푸코실락토오스와 분리 정제가 까다로운 락토오스 함량을 줄일 수 있다.
상기 락토오스 가수분해효소가 상기 미생물을 포함하는 배양액에 처리되는 경우, 락토오스 가수분해효소 처리 후 상기 미생물의 배양을 지속하는 것일 수 있다. 이 때, 상기 미생물은 탄소원으로 포도당 및 갈락토오스로 이루어지는 군에서 선택된 1종 이상을 사용 가능한 것일 수 있다. 상기 배양액에 락토오스 가수분해효소를 처리 후 미생물의 배양을 지속할 경우, 잔존당인 락토오스는 상기 락토오스 가수분해효소에 의해 분해되고, 락토오스가 분해되어 생성된 포도당 및/또는 갈락토오스를 상기 미생물이 탄소원으로 사용하여, 잔존당인 포도당 및/또는 갈락토오스가 제거되고, 최종 산물에서 포도당 및/또는 갈락토오스 함량이 낮아져, 2’-푸코실락토오스의 순도가 높아질 수 있다.
상기 락토오스 가수분해효소는 상기 배양액 내 2’-푸코실락토오스 함량 또는 농도의 최댓값을 도달한 시점 이후에 첨가되는 것일 수 있다. 상기 배양액 내 2’-푸코실락토오스 함량 또는 농도의 최댓값을 도달한 시점은, 2’-푸코실락토오스가 최대로 생산되는 시점, 2’-푸코실락토오스의 함량 또는 농도의 변화가 없는 시점, 또는 2’-푸코실락토오스의 함량 또는 농도가 감소하기 시작하는 시점을 의미하는 것일 수 있다.
일 예로, 상기 락토오스 가수분해효소는 상기 배양액의 2’-푸코실락토오스 함량의 증가율이 10% 이하, 9% 이하, 8% 이하, 7% 이하, 6% 이하, 5% 이하, 4% 이하, 3% 이하, 2% 이하, 또는 1% 이하일 때 첨가되는 것일 수 있다. 상기 2’-푸코실락토오스 함량의 증가율은 배양액 내의 2’-푸코실락토오스 함량의 시간에 따른 함량 변화율, 예를 들어 배양액 내의 2’-푸코실락토오스 농도의 시간에 따른 변화율 (mg/Ls)일 수 있다.
일 예로, 상기 락토오스 가수분해효소는 상기 배양액에서, 2’-푸코실락토오스 전환반응이 정상상태일 때 첨가되는 것일 수 있다. 상기 정상상태는 2’-푸코실락토오스 전환반응의 과도적 상태를 경과하여 시간의 흐름에 따라 변화하지 않는 상태로, 배양액 내 2’-푸코실락토오스 함량이 최댓값에 도달 후 일정한 상태일 수 있다.
상기 배양액에 락토오스 가수분해효소를 처리할 경우, 락토오스 가수분해효소에 의해 배양액 내 락토오스 함량이 감소하고, 포도당 및 갈락토오스의 함량은 증가할 수 있다.
예를 들어, 상기 락토오스 가수분해효소 처리 후 배양액은, 처리 전 배양액의 락토오스 함량 100중량%을 기준으로, 락토오스 함량이 5중량% 이하, 4중량% 이하, 3중량% 이하, 2중량% 이하, 1.5중량 % 이하, 1중량% 이하, 0.5중량% 이하, 0.4중량% 이하, 0.3중량% 이하, 0.2중량% 이하, 또는 0.1중량% 이하인 것일 수 있다. 이 때, 상기 락토오스 함량의 하한값이 특정되지 않더라도, 통상의 기술자가 상기 배양액에 락토오스 가수분해효소를 처리하여 락토오스의 분해가 일어난 뒤의 락토오스 함량을 명확히 이해할 수 있을 것이나, 예를 들어 상기 락토오스 함량의 하한값은 0중량% 이상, 0중량% 초과, 0.001중량% 이상, 0.005중량% 이상, 0.01중량% 이상, 0.05중량% 이상, 0.1중량% 이상, 0.5중량% 이상, 또는 1중량% 이상일 수 있으나, 이에 제한되는 것은 아니다.
본 발명의 일 예에 따른 2’-푸코실락토오스를 제조하는 방법은, 상기 미생물의 배양액에서 균체를 제거하여 상등액을 얻는 단계를 추가로 포함하는 것일 수 있다. 상기 균체 제거는 예를 들어 원심분리를 통해 제거될 수 있다. 일 예로, 원심분리를 통해 세포 잔해물 (cell debris)을 제거하는 것일 수 있다.
본 발명의 일 예에 따른 2’-푸코실락토오스를 제조하는 방법은, 상기 미생물의 배양액에서 균체를 제거하여 상등액을 얻고, 상기 상등액을 정제하여 2’-푸코실락토오스를 얻는 단계를 추가로 포함하는 것일 수 있다.
상기 정제는 활성탄 처리, 초미세여과 (Ultrafiltration), 나노여과 (Nanofiltration), 전기투석 (Electrodialysis), 및 이온교환수지 (Ion exchange)로 이루어지는 군에서 선택된 1종 이상의 공정을 포함하는 것일 수 있다.
상기 활성탄 처리 공정은 큰 사이즈의 단백질을 제거하고, 색도를 1차 조정할 수 있다. 상기 활성탄 처리 공정은 정제과정 중 초기에 수행될 수 있다. 활성탄 공정을 초기에 진행할 경우 이후 여과 시 큰 사이즈 단백질이 여과막에 걸려 막히는 파울링 (fouling) 현상을 지연할 수 있으며, 막의 사용 기간과 분리 효율을 상승시킬 수 있다.
상기 초미세여과 (Ultrafiltration) 공정은 작은 사이즈 (예를 들어 1kDa 이하)의 단백질을 제거하는 것일 수 있다. 상기 초미세여과 공정은 나노여과 (Nanofiltration) 공정 이전에 수행되는 것일 수 있다. 초미세여과 공정을 나노여과 공정 이전에 수행할 경우, 남아있는 단백질을 모두 제거하여 NF 여과막의 사용 기간이 늘어나며 압력 증가 없이 염류의 제거가 가능하다. 특히, 나노여과 공정은 여과액이 아닌 농축물을 사용하게 되므로 이전에 충분한 단백질 제거가 필요하다.
상기 나노여과 (Nanofiltration) 공정은 Sodium acetate, glycrol 등의 염류를 제거하는 것일 수 있다. 상기 나노여과 공정은 전기투석 (Electrodialysis) 공정 이전에 수행되는 것일 수 있다. 나노여과 공정을 전기투석 공정 이전에 진행하면 1차례 염류가 제거되어 전기투석 공정의 부하 (load)가 줄어들 수 있다. 또한, 전기투석 공정 시 초기 전도도 값이 너무 높으면 정제 후 전도도 값이 높아질 수 있으며, 나노여과 등을 이용하여 농축한 샘플을 전기투석 및 이온교환수지 정제에 이용하면 공정 시간과 용량이 단축될 수 있다.
상기 전기투석 (Electrodialysis) 공정은 Sodium citrate, glycrol 등의 염류를 제거하고, 전도도를 감소 (예를 들어 1mS 이하)하는 것일 수 있다. 전기투석 공정을 수행하면 이온교환 공정 전 염류 및 이온물질을 충분히 제거할 수 있으며, 처리 비용이 비싼 이온교환수지의 부하 (load)를 줄일 수 있다.
상기 이온교환수지 공정은 최종 전도도를 감소 (예를 들어 20uS 이하)하고, 색도를 2차 조정하는 것일 수 있다. 이온교환공정을 정제공정 중 마지막에 수행하면 마지막 소량의 이온물질을 충분히 제거할 수 있고, 마지막으로 색깔과 불순물을 깔끔하게 제거할 수 있다. 상기 이온교환수지는 양이온교환수지 및/또는 음이온교환수지를 포함할 수 있다. 상기 양이온교환수지는 강산성 양이온교환수지인 것일 수 있다. 예를 들어 양이온교환수지 (SCRB 혹은 CMP18) 또는 음이온교환수지 (AW30, WAS 또는 AMP24)를 사용할 수 있다.
상기 강산성 양이온교환수지는 넓은 pH 범위에서 실질적으로 완전히 이온화된 형태를 유지하여 약산성 양이온교환수지와 구별되며, 약산성 양이온교환수지는 좁은 pH 범위에서 이온화된 형태를 유지한다. 상기 강산성 양이온교환수지는 중합체 (예를 들어 폴리사카라이드) 매트릭스에 설포, 설포알킬 (예를 들어 설포메틸, 설포에틸 또는 설포프로필), 포스포 또는 포스포알킬 작용기가 결합되어 있는 것일 수 있다. 일 예로, 상기 강산성 양이온교환수지는 설포 또는 설포알킬 작용기를 가지는 것일 수 있다.
SCRB : 강산성, Polystyrene+DVB 모체, Sulfonate 교환기, Na 이온형
CMP18 : 강산성, Polystyrene+DVB 모체, Sulfonate 교환기, Na 이온형
AW30 : 약염기성, Polystyrene+DVB 모체, Tertiary amine 교환기, free base 이온형
AMP24 : 강염기성, Polystyrene+DVB 모체, Dimethylethanolammonium 교환기, Cl 이온형
본 발명의 일 예에 따른 2’-푸코실락토오스를 제조하는 방법은, 상기 상등액을 정제하는 단계 및/또는 상기 정제된 상등액을 농축하는 단계를 추가로 포함하는 것일 수 있다. 또는, 상기 상등액을 농축 또는 분무건조하여 2’-푸코실락토오스 분말을 얻는 단계를 추가로 포함하는 것일 수 있다.
상기 농축 공정은 희석된 정제물 (예를 들어 정제액)을 농축하는 것으로, 분무건조를 하기 위해 농축하는 것일 수 있다. 예를 들어, 정제액을 30 내지 80 Brix로 농축하는 것일 수 있다.
상기 분무건조 (Spray drying) 공정은 2’-푸코실락토오스 분말 (powder)을 제조하는 공정이며, 분무건조를 통해 2’-푸코실락토오스 분말 형태를 얻을 수 있다.
본 발명의 일 예에 따른 2’-푸코실락토오스를 제조하는 방법은 락토오스를 포함하는 배지에서 알파-1,2-푸코오스 전이효소를 가지는 미생물을 배양하고, 배양액에 락토오스 가수분해효소를 처리하여, 고순도의 2’-푸코실락토오스를 얻는 것일 수 있다. 예를 들어, 본 발명의 일 예에 따른 2’-푸코실락토오스를 제조하는 방법은 순도 86% 이상, 87% 이상, 88% 이상, 89% 이상, 90% 이상, 91% 이상, 92% 이상, 93% 이상, 94% 이상, 또는 95% 이상의 2’-푸코실락토오스를 얻는 것일 수 있다. 예를 들어, 본 발명의 일 예에 따른 2’-푸코실락토오스를 제조하는 방법은 당류 고형분 100중량% 기준으로 2’-푸코실락토오스 함량이 45중량% 이상, 50중량% 이상, 55중량% 이상, 60중량% 이상, 65중량% 이상, 70중량% 이상, 75중량% 이상, 80중량% 이상, 85중량% 이상, 86중량% 이상, 87중량% 이상, 88중량% 이상, 89중량% 이상, 90중량% 이상, 91중량% 이상, 92중량% 이상, 93중량% 이상, 94중량% 이상, 또는 95중량% 이상인 정제물을 얻는 것일 수 있다.
본 발명의 일 예에 따른 알파-1,2-푸코오스 전이효소를 가지는 미생물은 알파-1,2-푸코오스 전이효소를 발현 또는 분비하며, 상기 α-1,2-푸코오스 전이효소의 예시적인 아미노산 서열을 표 1에 나타내었다.
명명 | 서열 | 서열번호 |
Am2FT_2 | MNMERKTGLMNKKYVSPCFLPGMRLGNIMFTLAAACAHARTVGVECRVPWAYNDASLMLRSRLGGWVLPSTPCGTNEPPSWQEPSFAYCPVPSRIRTGGLRGYFQSARYFEGQEAFIRALFAPLTAEKEPGAVGIHIRLGDYRRLRDKHRILDPGFLRRAAGHLSSGKNRLVLFSDEPDEAAEMLARVPAFGRFALEIDRGAPCESLRRMTAMEELVMSCSSFSWWGAWLGNTRKVIVPRDWFVGGVEDYRDIYLPHWVTL | 1 |
Bm2FT | MKIVQISSGLGNQLFQYALYKRLSMNNNDVFLDVETSYQLNKNQHNGYEIERIFSIQPSHATKGMIDELADVDNRLINRLRRKLFGPKNSMYTETKEFSYDCEVFTKDGIYIKGYWQNYNYFKEIEDDLKNELVFKKALDLKNSHLINQMNKEISVSIHVRRGDYYLNKEYENKFGNIADLDYYLKAINFIKKEVDDPKFYVFSDDIKWAKENLNLTDNVTYVEHNKGSDSYKDMRLMTCCKHNIIANSTFSWWGAFLNENKNKIVIAPGKWINVEGVGGINLFPEGWIVY | 2 |
Bm2FT_2 | MGCIKRLFLYEYGGRCFLVIVKIKGGFGNQLFTYASAYAISQELQQNLIMDKVIYDLDYFRKFELPSLSLKYDQMLISKFVPNTKVKTLIYKVLRRLKLKGFTEVHEKKEFSFDENIYNLSGDIYLDGYWQNYRYFHKYYKDLSEMFVPRETPRKEVTDYITSLRGVNSVAMHVRRGDYKTFNGGKCLSLDYYIKAMEYFNSNDVQFYVFTDDIDFCEKNLPNSENINYVSRSEKLTDIEEFFIMKECKNFIIANSSFSWWAAYLSEQKADSLIVAPVVDMWKRDFYPDEWVALNTHLE | 3 |
Bm2FT_3 | MIIVQIKGGLGNQLFSYASAYGIARENETELIIDRYIYDTSYSLRKYMLDFFPEIDEALLLKYIPKKNKISQIMYKLIRKSKLKYKYKAQLFLEEEEFKFTRISTQNENLYLNGYWQSYVYFDKYRNDIIKKFTPLVSFNQDGNQLLNEIKSYNSVAIHVRRGDYINFKGGKCLDSSYYIKAMKHLYNLKGKNLFFYIFTDDVEYCKRIFKNVANVKFIGEEAKLSDFEEFTLMTHCKNLIIGNSSFSWWAAYLASCKDKAVIAPVVDMWTEDFYLPEWIKIKADLQ | 4 |
Bs2FT | MKIVHISSGLGNQMFQYALYKKLSLIQDNVFLDTITSYQLYPNQHNGYELEKVFTIKPRHASKELTYNLSDLDNSVTSRIRRKLIGSKKSMYIEHKEFEYDPNLFYQENIYIKGYWQNYDYFKDIENELKNDFTFQRALDEKNNNLAIKINNENSISIHVRRGDYYLNRKNQEKFGDIANLEYYSKAISYIKERIDNPKFYIFSDNVEWVKQNLNSLEEAVYIDYNVGNDSYKDMQLMSLCKHNIIANSSFSWWGAFLNKNMEKIVIAPGKWINMKGVKKVNLFPKDWIIY | 5 |
Bm2FT_4 | MIIVRVIGGLGNQMFQYALYKSLENEGKEVKLDLTGFGDYDLHNGYELNKIFNINENVATKDEINKLIKLPDNKVLSMIKRKFFSSTINYYSQDQFKYLSEIFQLDNVYLDGYWQSEKYFQGIKEVIRKEFKFKGEPNPKNIEMVKLMRGSNSVSIHFRRGDYISNPDAYKVHGGITTIHYYENAVKEIKSKVKEPKFFIFSDDIKWVKENFKLEDAFFIDWNTGSESYRDIELMSNCKHNIIANSTFSWWGAWLNKNKNKIVIAPNQWFNTIDTEDVIPDTWQCINTF | 6 |
Bt2FT | MNEIHVLLTGRLGNQLFQYAFARSLQKQYGGRIVCNTFDLDHRSEKSKVADQKFSYAMGDFKLDENVALEDAALPWYADFSSPLIKPVKKLFPRRYFDFMARRGYLMWQRTDYMPIPKLECEDVFAWGWWQDIRYFQDVQTELSDEVVPVTDPLPENQYIYNAASGEESVCISIRCGNYFNPTVKKLLYVCTPEYFRNAVESITKRLTHPKFIVFTDDVDWVKENIRFESAYPQYEFLYERGSDTVEEKIRMMTLCKHFIISNSTFSWWAQFLSKSENKIVIAPDRWFVDGRRIGLYMHGWTLIPAGQ | 7 |
Fp2FT | MIYVEMHGRLGNQMFQYAAARALQEKNNQPIMLSFRKVIGANTEGTAGWENSLKYFNVKPCEYYMGKKSLVTEYPVEYRLLCYAYALSYKPLMNNMNRWYEYQVKCCRFLDRFGIRWIANGYYDFHYNGLKNYLLNGSFESPKYFDSIRDKLLEEFTPREEERKENKRLYEQIRKRNSVCLSVRHFQLTGKQADMYDVCSLEYYQTAIRKMCELIENPLFVVFSDDIEWVKNTIDLSRVEVVYETPGNPVWEKLRLMYSCKNFIIPNSTFAWWAQYLSRNPDKYVLCPAKWFNNNFESPLIASQWVRIDREGNIVNE | 8 |
Gs2FT | MKIVKVIGGLGNQMFQYAFYRNLKAKFQEVKLDITAFETYKLHNGYELERVFDIKPEYATKKEIYPLTTNRNSKISKIKRRIFGGKETEYIEKDLKFDPEVFKVTGDVYFEGYWQTEKYFKEIEDLIRKDFQFKNPLTNKNLELSNKIKNENSVSIHVRRGDYYTSKKAERKHGNIATIEYYQKAVRKITEFVDNPVFYIFSDDIPWVKENLKLENEVIYVDWNKGLDSYIDMQLMSICKHNIIANSTFSWWGAWLNQNKNKIVIAPSRWINNKRLDTSDVIPKEWIKI | 9 |
Lg2FT | MLYVEMDGRCGNQLFHYAVARYIQLAIGNKEKLCLNFNKIFEKKDENNGWVDYLKDFKTVPYSYYSKSGTILKNESNFIQKIAIGLKAIQIKSLTKKSRQEQADKAEVGQRTLNKLGVYWVREGVNQIYPYKNNKILVSGICESNFIYEIQEQLQKELIPVTPVSSLNKSLLEKIDNCNSVCISVRRGDFFNNKNAKKYGVCSPEYYIRAKKYFDKKRLENTVYFCFSDDIEWCKENLKFTDKNVIFVSQEMPVYETLRLMSHCKHFILSNSTFSWWGQFLSEYKDKIVVSPARWNNDGYDTNLIDKNWILIDA | 10 |
Ll2FT | MIYVEIRGNLGNQLFIYATAKKIQKLTGQKIQLNTTTLNKYFPNYKFGLSEFIMEDPDCFIESYKKLPWFTNEYLLPIKIFKKILNKTPKINKILSDFFFKAFEKKGYFIWRGETFKKFSLGNHKNYYLSGFWQSEDYFYDIRDELLEIITPINSIRECNFELLNLIRNSESICVSIRRGDYVDNPKISAIYNVCDINYFIESVNEIKKNVVNVKVICFSDDVEWVKKNIKFDCETHYETYGNSLSEKVQLMSSCKHFVLSNSSFSWWTEFLSIRGGITIAPKNWYADEREADIYRKNWIYLEDKTEEE | 11 |
Ls2FT | MEEIHTLLTGRLGNQLFQYAFARNLQKQYGGQIYCDVYELEHRMSKVADEKFSYAMSGFKLDAGVIREDQAFPWYADFSNPVIKPIKKAMPRKYFELMARRGYLMWQRSDYMPIPVLDTQRVFASGWWQDIRYLQNVQEELSDEIVPITNPLQENRYIYDAAHDRDSVCISIRCGNYFNPTVKKLLYVCNPQYFHDSVKRISQMLAHPKFIVFTDDVSWVKEHLKFEDTYPQFEFLYERGCDTAEEKIRMMAMCNNFIISNSTFSWWAQFLSKNKEKIVIAPDKWFVDGRKIGLYMDGWTLVPAGR | 12 |
Ri2FT | MIAVKIGDGMGNQLFNYACGYAQARRDGDSLVLDISECDNSTLRDFELDKFHLKYDKKESFPNRNLGQKIYKNLRRALKYHVIKEREVYHNRDHRYDVNDIDPRVYKKKGLRNKYLYGYWQHLAYFEDYLNEITAMMTPAYEQSETVKKLQEEFKKTPTCAVHVRGGDIMGPAGAYFKHAMERMEQEKPGVRYIVFTNDMERAEEALAPVLESQKKDAVGQAENRLEFVSEMGEFSDVDEFFLMAACQNQILSNSTFSTWAAYLNQNPDKTVIMPDDLLSERMRQKNWIILK | 13 |
Te2FT (WP_011056838.1) |
MIIVHLCGGLGNQMFQYAAGLAAAHRIGSEVKFDTHWFDATCLHQGLELRRVFGLELPEPSSKDLRKVLGACVHPAVRRLLAGHFLHGLRPKSLVIQPHFHYWTGFEHLPDNVYLEGYWQSERYFSNIADIIRQQFRFVEPLDPHNAALMDEMQSGVSVSLHIRRGDYFNNPQMRRVHGVDLSEYYPAAVATMIEKTNAERFYVFSDDPQWVLEHLKLPVSYTVVDHNRGAASYRDMQLMSACRHHIIANSTFSWWGAWLNPRPDKVVIAPRHWFNVDVFDTRDLYCPGWIVL | 14 |
Fut C (Hp2FT) (WP_080473865.1) |
MAFKVVQICGGLGNQMFQYAFAKSLQKHSNTPVLLDITSFDWSDRKMQLELFPIDLPYASAKEIAIAKMQHLPKLVRDALKCMGFDRVSQEIVFEYEPKLLKPSRLTYFFGYFQDPRYFDAISPLIKQTFTLPPPPENNKNNNKKEEEYQCKLSLILAAKNSVFVHIRRGDYVGIGCQLGIDYQKKALEYMAKRVPNMELFVFCEDLEFTQNLDLGYPFMDMTTRDKEEEAYWDMLLMQSCQHGIIANSTYSWWAAYLIENPEKIIIGPKHWLFGHENILCKEWVKIESHFEVKSQKYNA | 15 |
Am2FT_1 (WP_081429121.1) |
MAGHSCGKYANSWRKYAGISRFNPFPCLNMAKGKIIVMRLFGGLGNQLFQYAFLFALSRQGGKARLETSSYEHDDKRVCELHHFRVSLPIEGGPPPWAFRKSRIPACLRSLFAAPKYPHFREEKRHGFDPGLAAPPRRHTYFKGYFQTEQYFLHCREQLCREFRLKTPLTPENARILEDIRSCCSISLHIRRTDYLSNPYLSPPPLEYYLRSMAEMEGRLRAAGAPQESLRYFIFSDDIEWARQNLRPALPHVHVDINDGGTGYFDLELMRNCRHHIIANSTFSWWAAWLNEHAEKIVIAPRIWFNREEGDRYHTDDALIPGSWLRI | 16 |
상기 α-1,2-푸코오스 전이효소는 Biosafety level 1 균주에서 유래한 것일 수 있다. 예를 들어, 상기 α-1,2-푸코오스 전이효소는 서열번호 1 내지 서열번호 16으로 이루어지는 군에서 선택된 1종 이상의 아미노산 서열을 포함하는 것일 수 있다. 예를 들어, 상기 α-1,2-푸코오스 전이효소는 서열번호 1 내지 서열번호 5로 이루어지는 군에서 선택된 1종 이상의 아미노산 서열을 포함하는 것일 수 있다. 예를 들어, 상기 α-1,2-푸코오스 전이효소는 서열번호 1, 서열번호 2, 서열번호 3, 서열번호 4, 또는 서열번호 5의 아미노산 서열을 포함하는 것일 수 있다. 예를 들어, 상기 α-1,2-푸코오스 전이효소는 서열번호 1, 서열번호 2, 서열번호 3, 서열번호 4, 또는 서열번호 5의 아미노산 서열로 이루어지는 것일 수 있다.
표 1에서 서열번호 1의 푸코오스 전이효소는 아커만시아 무시니필라 유래이며, Am2FT_2로 명명하였다. 서열번호 2 내지 4의 푸코오스 전이효소는 바실러스 메가테리움 유래이며, 각각 Bm2FT, Bm2FT_2, 및 Bm2FT_3로 명명하였다. 서열번호 5의 푸코오스 전이효소는 바실러스 속 유래이며, Bs2FT로 명명하였다.
서열번호 1 내지 5의 2’-푸코실락토오스 생산 활성을 확인한 결과, Am2FT_2는 약 5 (mg/L), Bm2FT는 약 15 (mg/L), Bm2FT_2는 약 3 (mg/L), Bm2FT_3는 약 4 (mg/L), 및 Bs2FT는 약 1 (mg/L)의 2’-푸코실락토오스를 생성하여, 2FL 생산 활성을 가졌다. 상기 2FL 생산 활성은 다음과 같은 과정으로 확인하였다: 서열번호 1 내지 5의 α-1,2-푸코오스 전이효소 플라스미드를 각각 바실러스 메가테리움에 transformation 후 37℃에서 키웠다. 각각의 plate 에서 2개의 colony를 접종하여 overnight seed culture를 진행하였다. seed 200 uL를 22mM lactose가 첨가된 4mL 배지에 첨가하여 30℃에서 반응을 진행하였다. 20h 후 HPLC 로 분석하였다.
본 발명의 일 예에 따른 알파-1,2-푸코오스 전이효소를 가지는 미생물은 탄소원으로 포도당 및 갈락토오스로 이루어지는 군에서 선택된 1종 이상을 사용 가능한 것일 수 있다. 이 때, 락토오스 가수분해효소를 배양액에 처리 후 상기 미생물의 배양을 지속할 경우, 상기 미생물이 락토오스의 분해산물인 포도당 및/또는 갈락토오스를 탄소원으로 사용하여, 락토오스, 포도당 및 갈락토오스로 이루어지는 군에서 선택된 1종 이상의 잔존당을 배양액 내에서 효과적으로 제거하고, 2’-푸코실락토오스 생산량도 높일 수 있다.
상기 알파-1,2-푸코오스 전이효소를 가지는 미생물은 하기 (1) 내지 (4)로 이루어지는 군에서 선택된 1종 이상의 특징을 가지는 것일 수 있다:
(1) LacZ 유전자가 결실됨,
(2) 푸코오스 합성 유전자를 발현함,
(3) 락토오스 막 수송 단백질을 발현함, 및
(4) 포도당 및/또는 갈락토오스를 탄소원으로 사용함.
상기 푸코오스 합성 유전자는 GDP-D-만노오스-4,6-데하이드라타아제 (GDP-D-mannose-4,6-dehydratase), GDP-L-푸코오스 신타아제 (GDP-L-fucose synthase), 포스포만노뮤타아제 (phosphomannomurase), 및 GTP 만노오스-1-포스페이트 구아닐릴트랜스퍼라아제 (GTP-mannose-1-phosphate guanylyltransferase)로 이루어지는 군에서 선택된 1종 이상인 것일 수 있다.
상기 락토오스 막 수송 단백질은 Lac12 및 LacY로 이루어지는 군에서 선택된 1종 이상인 것일 수 있다.
본 발명의 일 예에 따른 알파-1,2-푸코오스 전이효소를 가지는 미생물은 바실러스 속 (Bacillus sp.) 미생물, 코리네박테리움 속 (Corynebacterium sp.) 미생물, 대장균 속 (Escherichia sp.) 미생물, 및 효모 (yeast)로 이루어지는 군에서 선택된 1종 이상인 것일 수 있다.
상기 바실러스 속 (Bacillus sp.) 미생물은 바실러스 메가테리움 (Bacillus megaterium), 바실러스 서브틸리스 (Bacillus subtilis), 바실러스 세레우스 (Bacillus cereus), 바실러스 코아귤런스 (Bacillus coagulans), 바실러스 리체니포르미스 (Bacillus licheniformis), 및 바실러스 스테아로테르모필루스 (Bacillus stearothermophilus)로 이루어지는 군에서 선택된 1종 이상인 것일 수 있다.
상기 코리네박테리움 속 (Corynebacterium sp.) 미생물은 코리네박테리움 글루타미쿰 (Corynebacterium glutatamicum) 일 수 있다.
상기 대장균 속 (Escherichia sp.) 미생물은 대장균 (Escherichia coli) 일 수 있다.
상기 효모 (yeast)는 사카로미세스 세레비시아 (Saccharomyces cerevisiae), 및 캔디다 유틸리스 (Candida utilis)로 이루어지는 군에서 선택된 1종 이상인 것일 수 있다.
본 발명은 2’-푸코실락토오스를 생산하는 과정에서 락토오스 가수분해효소를 처리하여, 락토오스를 효과적으로 제거하여 2’-푸코실락토오스 생산량을 높이고, 발효액 내 단백질도 99% 이상 제거할 수 있으며, 발효액 내 배양 부산물과 염류 등을 제거하여 고순도의 2’-푸코실락토오스를 제조할 수 있다.
도 1은 본 발명의 일 예에 따라 얻어진 2’-푸코실락토오스의 순도를 확인한 도면이다.
이하, 본 발명을 하기의 실시예에 의하여 더욱 상세히 설명한다. 그러나 이들 실시예는 본 발명을 예시하기 위한 것일 뿐이며, 본 발명의 범위가 이들 실시예에 의하여 한정되는 것은 아니다.
실시예 1. α-1,2-푸코오스 전이효소를 가지는 미생물 제조
락토오스로부터 2’-푸코실락토오스 전환능을 가지는 미생물을 제조하기 위해 예시적으로 Biosafety level 1 균주인 바실러스 메가테리움 (Bacillus megaterium) 14581 (한국 미생물 보존 센터 (KCCM) 기탁번호 40441)을 한국 미생물 보존 센터 (KCCM)에서 입수하여 host로 사용하였다. α-1,2-푸코오스 전이효소의 예시적인 아미노산 서열은 서열번호 1 내지 16에 나타나 있으며, 대표적으로 서열번호 2의 아미노산 서열을 가지는 α-1,2-푸코오스 전이효소(alpha-1,2-fucosyltranferase)를 사용하였다. 바실러스 메가테리움 14581 유전자 내에 b-galactosidase (이하 LacZ)를 homologous recombination 방법을 통해 제거하였고, genome sequencing 을 통해 LacZ 유전자가 제거된 것을 확인하였다.
벡터 형태로 α-1,2-푸코오스 전이효소를 과발현하기 위해, 종래에 주로 사용되는 프로모터인 자일로스 유도 프로모터 (이하 pXyl)를 대체하는 p3610, p12455, 또는 p24930 항시 발현 프로모터를 서열번호 2의 아미노산 서열을 가지는 효소 (Bm2FT)를 발현하도록 플라스미드를 제작하고, 이를 상기 제조한 LacZ 결실 균주에 형질전환하여 2’-푸코실락토오스 전환능을 가지는 균주를 제조하여 실험에 사용하였다.
젖당을 세포 내에 더 많이 도입하기 위하여 클루이베로마이세스 락티스 (Kluyveromyces lactis) 유래의 락토오스 막 수송 단백질 (이하 Lac12) 또는 바실러스 메가테리움 유래의 락토오스 막 수송 단백질 (이하 LacY)을 플라스미드 형태로 항시 발현 프로모터 p12455가 도입된 △LacZ 바실러스 메가테리움에 도입하였다.
바실러스 메가테리움 14581 균주의 GDP-fuc 합성 효소 4종인 GDP-D-만노오스-4,6-데하이드라타아제 (이하 Gmd), GDP-L-푸코오스 신타아제 (이하 WcaG), 포스포만노뮤타아제 (이하 Hypo 또는 ManB) 및 GTP 만노오스-1-포스페이트 구아닐릴트랜스퍼라아제 (이하 ManC) 4종 효소를 항시발현 프로모터를 사용하여 과발현 되도록 플라스미드 형태로 형질전환하여 생산성을 향상시키고자 하였다. 구체적으로, 50ul 플라스미드를 lysozme을 처리한 500ml b.megaterium protoplast와 섞었다. PEG-P 1.5mL이 들어있는 15mL 팔콘에 5mL SMMP 를 첨가하고 조심히 팔콘을 굴려 섞었다. 1300g에서 10분 원심 분리하여 세포 수거 후 SMMP에 세포를 풀어주어 1.5mL 37C에서 250rpm shaking 하여 형질전환을 완료하였다.
비교예 1. 모유올리고당 제조 (1)
(1) 종균배양
-70℃ 온도에서 냉동 보관된 상기 실시예 1에서 제조한 Bacillus megaterium 유래 균주를 3ml 액체배지의 Test-tube에 100uL 접종하여, 30℃에서 240rpm으로 12-18시간 배양하였다. 배양이 완료된 3mL 액체 배양액은 다시 멸균 상태인 250mL 삼각플라스크의 50ml 액체배지에 접종하여, 30℃에서 240rpm으로 12~16시간 배양하였다. 종균배양에 사용한 배지 조성은 yeast extract 5 g/L, Tryptone 10 g/L 및 NaCl 10 g/L를 포함하였다.
(2) 본배양
멸균된 5L 용량의 자발효기 (jar fermentor)에서 배양이 완료된 100mL 배양액을 본배양 배지 2L에 접종하여 30℃에서 500-800rpm, 1v/v/m 조건으로 배양을 진행하였다. 상기 본배양 배지의 조성을 표 2에 나타내었으며, 본배양 배지에 첨가된 100X TMS (Trace Metal Solution)의 조성을 표 3에 나타내었다.
배양 초기에 적절한 당 농도를 설정하여 배양하고, 미생물의 성장 속도에 따라 고농도의 당을 점진적으로 주입하여 배양액 내에 낮은 당 농도를 유지하는 방법을 사용하였다. 당의 첨가 시기, 방법 및 첨가량에 따라 다양한 유가식 배양방법을 사용할 수 있으며, 본 실험에서는 pH 유지 당 공급 (pH stat feeding)을 사용하였다. Feeding 시작 전에 15 g/L의 락토오스를 추가 공급하였으며, 추가 용액 (feeding solution)의 조성은 Glucose 750g/L 및 MgSO4·7H2O 15 g/L을 포함하였다. 배양 초기에 배양액의 pH가 7.0 내지 7.2 범위로 유지되도록 탄소원, 수산화나트륨 또는 암모니아수와 같은 염기성 용액을 공급하였다.
배양이 완료된 후 원심분리기를 이용하여 배양액에서 균체를 제거하고, 상등액을 회수하여 발효액 (fermentation broth)을 모유올리고당 정제에 사용하였다.
성분 | 농도 (g/L) |
Glucose | 10 |
Lactose | 15 |
MgSO4-7H2O | 0.3 |
Yeast extract | 3 |
(NH4)2SO4 | 1 |
K2HPO4 | 12 |
KH2PO4 | 3 |
NaCl | 0.1 |
CaCl2-2H2O | 0.015 |
FeSO4-7H2O | 0.015 |
Thaimine | 0.010 |
100X TMS | 10ml |
성분 | 농도 (g/L) |
Tri-sodium citrate | 20 |
CaCl2.2H2O | 11.5 |
FeSO4.7H2O | 8.3 |
MnCl2.4H2O | 3.2 |
Zn(CH3COO)2.2H2O | 1.68 |
CuCl2.2H2O | 0.302 |
CoCl2.6H2O | 0.534 |
H3BO3 | 0.666 |
Na2MoO4.2H2O | 0.534 |
Thiamine | 0.534 |
1N HCl 원액 (ml) | 100 |
dH2O | up to 1L |
실시예 2. 모유올리고당 제조 (2)
비교예 1과 같은 방법으로 균주를 배양하고, 배양 완료 후 상등액을 회수하고, 상등액에 락토오스 가수분해효소를 처리하여 잔존 락토오스를 제거하였다. 구체적으로, 상기 회수된 상등액에 락토오스 가수분해효소 (Novozymes, Lactozym® 6500L)를 50℃에서 16시간 이상 처리하였고, 락토오스가 모두 분해되어 포도당 및 갈락토오스가 생성되는 것을 HPLC 분석을 통해 확인하였다.
상기 락토오스가 분해된 배양액을, 원심분리기를 사용하여 8,000rpm (11,000g)으로 8℃ 온도에서 15분 간 수행하여 원심분리를 수행하여 균체를 제거하고, 상등액을 회수하여 발효액 (fermentation broth)을 모유올리고당 정제에 사용하였다.
실시예 3. 모유올리고당 제조 (3)
비교예 1과 같은 방법으로 균주를 배양하고, 2’-푸코실락토오스 생산량의 증가가 없는 배양 후기에 락토오스가수분해효소 (Novozymes, Lactozym® 6500L)를 처리하고 이후 12-24시간 동안 배양을 지속하여 추가 배양을 실시하였다. 추가 배양이 진행되는 동안 락토오스는 분해되고, 생성된 포도당 및 갈락토오스는 2’-FL 생산 균주에 의해 소모되는 것을 HPLC 분석을 통해 확인하였다.
잔존당이 모두 제거된 배양액은 원심분리기를 사용하여 8,000rpm (11,000g)으로 8℃ 온도에서 15분 간 수행하여 원심분리를 수행하여 균체를 제거하여 상등액을 회수하여 발효액 (fermentation broth)을 모유올리고당 정제에 사용하였다.
실시예 4. 2’-푸코실락토오스 분리 정제
비교예 1, 실시예 2 및 실시예 3에서 얻은 상등액을 활성탄 처리, 초미세여과(Ultrafiltration), 나노여과 (Nanofiltration), 전기투석 (Electrodialysis), 및 이온교환수지 (Ion exchange) 공정 순서로 2’-푸코실락토오스를 분리 정제하였다.
구체적으로, 비교예 1, 실시예 2 및 실시예 3에서 얻은 발효액에 활성탄 (KB-EVN, 4% (고형분의 10%))을 투입 후, 70℃ 온도에서 30분 교반하여 수행하였다. 그 후 7,000rpm에서 20분간 원심분리한 다음 여과 (필터 사이즈: 1μm, 0.45μm)하여 활성탄을 제거하였다.
이어서, 단백질을 농축하여 제거하기 위해, 초미세여과기 (MILLIPORE, ProFlux M12)를 사용하여 30k&10kDa 필터, 135psi 압력 조건 하에서 초미세여과를 수행하였다. 다음으로, 나노여과기 (퓨어테크피앤티)를 사용하여 200-300Da, 145-150psi 조건 하에서, 상기 초미세여과공정을 거친 산물에 대해 나노여과를 수행하였다. 다음으로, 전기투석기 (INNOMEDITECH, PS520)를 사용하여 전기투석을 수행하였다 (정전압 방식: 1V/cell, 20cells, 총 20V). 전기투석을 완료한 샘플을 양이온 수지(SCRB), 음이온 수지(AW30), 혼합 수지(SCRB, AMP24)를 각각 패킹한 컬럼에 연속해서 흘려 이온교환을 수행하였다.
이온교환수지 통액 후 굴절당도계 (ATAGO Digital Regractometer)를 사용하여 당도를 측정한 결과 30 내지 50 brix로 측정되었다. 또한, 상기 각 분리 정제 공정 단계를 수행한 뒤 실시예 5의 방법에 따라 2’-푸코실락토오스의 순도를 측정하였다.
실시예 5. 2’-푸코실락토오스 분리 정제에 따른 순도 분석
실시예 4의 각 분리 정제 공정 단계를 수행한 뒤 2’-푸코실락토오스의 순도 (중량%) 변화를 측정하여 표 4에 나타냈다. 각 분리 정제 공정 단계별 성분 조성을 HPLC-RI로 측정하였고, 분석 조건은 다음과 같았다:
장비 : HPLC-RI (Waters)
이동상 : 5mM H2SO4
유속 : 0.6mL/min
오븐온도 : 50℃
Column : Rezex ROA Organic Acid H+ 8% (Phenomenex)
정제단계 | 비교예 1 | 실시예 2 | 실시예 3 |
Fermentation broth | 17.70 | 17.57 | 17.52 |
Active carbon | 17.76 | 17.76 | 18.56 |
Ultrafiltration | 17.56 | 18.13 | 18.08 |
Nanofiltration | 40.09 | 72.30 | 67.02 |
Electrodialysis | 42.51 | 74.43 | 94.03 |
Ion exchange | 44.25 | 85.17 | 95.24 |
표 4에 나타난 바와 같이, 2’-푸코실락토오스 전환반응 완료 후 배양액의 2’-FL 함량은 비교예 1과 실시예 1 및 2가 유사하였다. 그러나, 분리정제 과정을 거치면서 2’-FL 순도 차이가 나타났으며, 나노필터링 공정이후 실시예 2 및 3의 배양액은 45% 이상의 2’-FL 순도를 달성하였다. 특히, 실시예 3의 배양 상등액은 전기투석과 이온정제 공정을 수행한 후에는 각각 94% 이상의 2’-FL 순도를 달성하여 더욱 바람직한 결과를 나타냈다. 구체적으로, 실시예 3의 배양액은 2’-FL 최대 생산량에 도달한 때에 락타아제 처리를 통해 락토오스를 분해하고, 락토오스 분해산물인 포도당 및 갈락토오스를 소모하는 2’-푸코실락토오스 전환 미생물에 의해 2’-FL 이외의 당류가 제거되어, 90% 이상의 고순도 2’- 푸코실락토오스를 제조할 수 있었다.
실시예 6. 분리 정제에 따른 당류 분석
실시예 4의 분리 정제 공정 단계를 수행한 뒤 당류 고형분 100중량%를 기준으로 각 당류의 함량을 표 5에 나타냈다.
당 비율 (%) | 2’-FL | 락토오스 | 포도당 | 갈락토오스 |
비교예 1 | 44.25 | 55.75 | 0 | 0 |
실시예 2 | 85.17 | 3.37 | 3.66 | 7.8 |
실시예 3 | >95 | 0 | 0 | 0 |
표 5에 나타난 바와 같이, 비교예 1에 비해 락타아제를 처리한 실시예 2 및 3은 종래에 2’-푸코실락토오스와 분리 정제가 어려웠던 락토오스가 효율적으로 제거되었다. 또한, 실시예 3은 배양 후기에 락타아제를 처리하고 추가 배양을 수행하여 락토오스, 포도당 및 갈락토오스가 소모되어 배양액 내에서 모두 제거되고, 정제완료 후 2’-FL 이외의 잔여당 함량이 최소화되고, 최종 산물의 2’-FL 함량이 90중량% 이상으로 매우 높았다.
실시예 7. 분리 정제에 따른 단백질 함량 분석
실시예 3에서 얻은 상등액의 각 분리 정제 공정 단계를 수행한 뒤 단백질 함량을 표 8에 나타냈다. 표 7에 나타난 바와 같이, 정제를 진행함에 따라 단백질은 AC, UF 공정에서 99% 이상 제거되었다.
단계 | 단백질 | |
농도(g/L) | 수율(%) | |
Fermentation broth | 3.46 | 100 |
Active carbon | 0.35 | 9.82 |
Ultrafiltration | 0.01 | 0.58 |
Nanofiltration | 0.06 | 0.56 |
Electrodialysis | 0.02 | 0.11 |
Ion exchange | 0.01 | 0.04 |
실시예 8. 2’-푸코실락토오스 분무건조
실시예 3의 상등액에 대해 실시예 4의 분리 정제 공정을 완료하고, 얻어진 산물을 분무건조하여 2’-푸코실락토오스의 분말을 제조하였다.
구체적으로, 실시예 5에서 제조한 이온정제액을 분무건조에 적합한 40-70 brix까지 농축하고, 분무건조기 (Yamato Spray Dryer, ADL311)를 사용하여 건조 분말을 제조하였다. 분무건조는 inlet 온도 140-150℃, outlet 온도 70-75℃, automizing air는 0.15, 펌프 속도는 1 mL/min 조건에서 진행하였다.
상기 얻어진 건조 분말을 용해 후 HPLC 분석을 실시하였고, 도 1과 같이 순도 95% 이상의 2’-FL을 확인하였다.
<110> SAMYANG CORPORATION
<120> Method for preparing 2'- Fucosyllactose
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Met Asn Met Glu Arg Lys Thr Gly Leu Met Asn Lys Lys Tyr Val Ser
1 5 10 15
Pro Cys Phe Leu Pro Gly Met Arg Leu Gly Asn Ile Met Phe Thr Leu
20 25 30
Ala Ala Ala Cys Ala His Ala Arg Thr Val Gly Val Glu Cys Arg Val
35 40 45
Pro Trp Ala Tyr Asn Asp Ala Ser Leu Met Leu Arg Ser Arg Leu Gly
50 55 60
Gly Trp Val Leu Pro Ser Thr Pro Cys Gly Thr Asn Glu Pro Pro Ser
65 70 75 80
Trp Gln Glu Pro Ser Phe Ala Tyr Cys Pro Val Pro Ser Arg Ile Arg
85 90 95
Thr Gly Gly Leu Arg Gly Tyr Phe Gln Ser Ala Arg Tyr Phe Glu Gly
100 105 110
Gln Glu Ala Phe Ile Arg Ala Leu Phe Ala Pro Leu Thr Ala Glu Lys
115 120 125
Glu Pro Gly Ala Val Gly Ile His Ile Arg Leu Gly Asp Tyr Arg Arg
130 135 140
Leu Arg Asp Lys His Arg Ile Leu Asp Pro Gly Phe Leu Arg Arg Ala
145 150 155 160
Ala Gly His Leu Ser Ser Gly Lys Asn Arg Leu Val Leu Phe Ser Asp
165 170 175
Glu Pro Asp Glu Ala Ala Glu Met Leu Ala Arg Val Pro Ala Phe Gly
180 185 190
Arg Phe Ala Leu Glu Ile Asp Arg Gly Ala Pro Cys Glu Ser Leu Arg
195 200 205
Arg Met Thr Ala Met Glu Glu Leu Val Met Ser Cys Ser Ser Phe Ser
210 215 220
Trp Trp Gly Ala Trp Leu Gly Asn Thr Arg Lys Val Ile Val Pro Arg
225 230 235 240
Asp Trp Phe Val Gly Gly Val Glu Asp Tyr Arg Asp Ile Tyr Leu Pro
245 250 255
His Trp Val Thr Leu
260
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Met Lys Ile Val Gln Ile Ser Ser Gly Leu Gly Asn Gln Leu Phe Gln
1 5 10 15
Tyr Ala Leu Tyr Lys Arg Leu Ser Met Asn Asn Asn Asp Val Phe Leu
20 25 30
Asp Val Glu Thr Ser Tyr Gln Leu Asn Lys Asn Gln His Asn Gly Tyr
35 40 45
Glu Ile Glu Arg Ile Phe Ser Ile Gln Pro Ser His Ala Thr Lys Gly
50 55 60
Met Ile Asp Glu Leu Ala Asp Val Asp Asn Arg Leu Ile Asn Arg Leu
65 70 75 80
Arg Arg Lys Leu Phe Gly Pro Lys Asn Ser Met Tyr Thr Glu Thr Lys
85 90 95
Glu Phe Ser Tyr Asp Cys Glu Val Phe Thr Lys Asp Gly Ile Tyr Ile
100 105 110
Lys Gly Tyr Trp Gln Asn Tyr Asn Tyr Phe Lys Glu Ile Glu Asp Asp
115 120 125
Leu Lys Asn Glu Leu Val Phe Lys Lys Ala Leu Asp Leu Lys Asn Ser
130 135 140
His Leu Ile Asn Gln Met Asn Lys Glu Ile Ser Val Ser Ile His Val
145 150 155 160
Arg Arg Gly Asp Tyr Tyr Leu Asn Lys Glu Tyr Glu Asn Lys Phe Gly
165 170 175
Asn Ile Ala Asp Leu Asp Tyr Tyr Leu Lys Ala Ile Asn Phe Ile Lys
180 185 190
Lys Glu Val Asp Asp Pro Lys Phe Tyr Val Phe Ser Asp Asp Ile Lys
195 200 205
Trp Ala Lys Glu Asn Leu Asn Leu Thr Asp Asn Val Thr Tyr Val Glu
210 215 220
His Asn Lys Gly Ser Asp Ser Tyr Lys Asp Met Arg Leu Met Thr Cys
225 230 235 240
Cys Lys His Asn Ile Ile Ala Asn Ser Thr Phe Ser Trp Trp Gly Ala
245 250 255
Phe Leu Asn Glu Asn Lys Asn Lys Ile Val Ile Ala Pro Gly Lys Trp
260 265 270
Ile Asn Val Glu Gly Val Gly Gly Ile Asn Leu Phe Pro Glu Gly Trp
275 280 285
Ile Val Tyr
290
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Met Gly Cys Ile Lys Arg Leu Phe Leu Tyr Glu Tyr Gly Gly Arg Cys
1 5 10 15
Phe Leu Val Ile Val Lys Ile Lys Gly Gly Phe Gly Asn Gln Leu Phe
20 25 30
Thr Tyr Ala Ser Ala Tyr Ala Ile Ser Gln Glu Leu Gln Gln Asn Leu
35 40 45
Ile Met Asp Lys Val Ile Tyr Asp Leu Asp Tyr Phe Arg Lys Phe Glu
50 55 60
Leu Pro Ser Leu Ser Leu Lys Tyr Asp Gln Met Leu Ile Ser Lys Phe
65 70 75 80
Val Pro Asn Thr Lys Val Lys Thr Leu Ile Tyr Lys Val Leu Arg Arg
85 90 95
Leu Lys Leu Lys Gly Phe Thr Glu Val His Glu Lys Lys Glu Phe Ser
100 105 110
Phe Asp Glu Asn Ile Tyr Asn Leu Ser Gly Asp Ile Tyr Leu Asp Gly
115 120 125
Tyr Trp Gln Asn Tyr Arg Tyr Phe His Lys Tyr Tyr Lys Asp Leu Ser
130 135 140
Glu Met Phe Val Pro Arg Glu Thr Pro Arg Lys Glu Val Thr Asp Tyr
145 150 155 160
Ile Thr Ser Leu Arg Gly Val Asn Ser Val Ala Met His Val Arg Arg
165 170 175
Gly Asp Tyr Lys Thr Phe Asn Gly Gly Lys Cys Leu Ser Leu Asp Tyr
180 185 190
Tyr Ile Lys Ala Met Glu Tyr Phe Asn Ser Asn Asp Val Gln Phe Tyr
195 200 205
Val Phe Thr Asp Asp Ile Asp Phe Cys Glu Lys Asn Leu Pro Asn Ser
210 215 220
Glu Asn Ile Asn Tyr Val Ser Arg Ser Glu Lys Leu Thr Asp Ile Glu
225 230 235 240
Glu Phe Phe Ile Met Lys Glu Cys Lys Asn Phe Ile Ile Ala Asn Ser
245 250 255
Ser Phe Ser Trp Trp Ala Ala Tyr Leu Ser Glu Gln Lys Ala Asp Ser
260 265 270
Leu Ile Val Ala Pro Val Val Asp Met Trp Lys Arg Asp Phe Tyr Pro
275 280 285
Asp Glu Trp Val Ala Leu Asn Thr His Leu Glu
290 295
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Met Ile Ile Val Gln Ile Lys Gly Gly Leu Gly Asn Gln Leu Phe Ser
1 5 10 15
Tyr Ala Ser Ala Tyr Gly Ile Ala Arg Glu Asn Glu Thr Glu Leu Ile
20 25 30
Ile Asp Arg Tyr Ile Tyr Asp Thr Ser Tyr Ser Leu Arg Lys Tyr Met
35 40 45
Leu Asp Phe Phe Pro Glu Ile Asp Glu Ala Leu Leu Leu Lys Tyr Ile
50 55 60
Pro Lys Lys Asn Lys Ile Ser Gln Ile Met Tyr Lys Leu Ile Arg Lys
65 70 75 80
Ser Lys Leu Lys Tyr Lys Tyr Lys Ala Gln Leu Phe Leu Glu Glu Glu
85 90 95
Glu Phe Lys Phe Thr Arg Ile Ser Thr Gln Asn Glu Asn Leu Tyr Leu
100 105 110
Asn Gly Tyr Trp Gln Ser Tyr Val Tyr Phe Asp Lys Tyr Arg Asn Asp
115 120 125
Ile Ile Lys Lys Phe Thr Pro Leu Val Ser Phe Asn Gln Asp Gly Asn
130 135 140
Gln Leu Leu Asn Glu Ile Lys Ser Tyr Asn Ser Val Ala Ile His Val
145 150 155 160
Arg Arg Gly Asp Tyr Ile Asn Phe Lys Gly Gly Lys Cys Leu Asp Ser
165 170 175
Ser Tyr Tyr Ile Lys Ala Met Lys His Leu Tyr Asn Leu Lys Gly Lys
180 185 190
Asn Leu Phe Phe Tyr Ile Phe Thr Asp Asp Val Glu Tyr Cys Lys Arg
195 200 205
Ile Phe Lys Asn Val Ala Asn Val Lys Phe Ile Gly Glu Glu Ala Lys
210 215 220
Leu Ser Asp Phe Glu Glu Phe Thr Leu Met Thr His Cys Lys Asn Leu
225 230 235 240
Ile Ile Gly Asn Ser Ser Phe Ser Trp Trp Ala Ala Tyr Leu Ala Ser
245 250 255
Cys Lys Asp Lys Ala Val Ile Ala Pro Val Val Asp Met Trp Thr Glu
260 265 270
Asp Phe Tyr Leu Pro Glu Trp Ile Lys Ile Lys Ala Asp Leu Gln
275 280 285
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Met Lys Ile Val His Ile Ser Ser Gly Leu Gly Asn Gln Met Phe Gln
1 5 10 15
Tyr Ala Leu Tyr Lys Lys Leu Ser Leu Ile Gln Asp Asn Val Phe Leu
20 25 30
Asp Thr Ile Thr Ser Tyr Gln Leu Tyr Pro Asn Gln His Asn Gly Tyr
35 40 45
Glu Leu Glu Lys Val Phe Thr Ile Lys Pro Arg His Ala Ser Lys Glu
50 55 60
Leu Thr Tyr Asn Leu Ser Asp Leu Asp Asn Ser Val Thr Ser Arg Ile
65 70 75 80
Arg Arg Lys Leu Ile Gly Ser Lys Lys Ser Met Tyr Ile Glu His Lys
85 90 95
Glu Phe Glu Tyr Asp Pro Asn Leu Phe Tyr Gln Glu Asn Ile Tyr Ile
100 105 110
Lys Gly Tyr Trp Gln Asn Tyr Asp Tyr Phe Lys Asp Ile Glu Asn Glu
115 120 125
Leu Lys Asn Asp Phe Thr Phe Gln Arg Ala Leu Asp Glu Lys Asn Asn
130 135 140
Asn Leu Ala Ile Lys Ile Asn Asn Glu Asn Ser Ile Ser Ile His Val
145 150 155 160
Arg Arg Gly Asp Tyr Tyr Leu Asn Arg Lys Asn Gln Glu Lys Phe Gly
165 170 175
Asp Ile Ala Asn Leu Glu Tyr Tyr Ser Lys Ala Ile Ser Tyr Ile Lys
180 185 190
Glu Arg Ile Asp Asn Pro Lys Phe Tyr Ile Phe Ser Asp Asn Val Glu
195 200 205
Trp Val Lys Gln Asn Leu Asn Ser Leu Glu Glu Ala Val Tyr Ile Asp
210 215 220
Tyr Asn Val Gly Asn Asp Ser Tyr Lys Asp Met Gln Leu Met Ser Leu
225 230 235 240
Cys Lys His Asn Ile Ile Ala Asn Ser Ser Phe Ser Trp Trp Gly Ala
245 250 255
Phe Leu Asn Lys Asn Met Glu Lys Ile Val Ile Ala Pro Gly Lys Trp
260 265 270
Ile Asn Met Lys Gly Val Lys Lys Val Asn Leu Phe Pro Lys Asp Trp
275 280 285
Ile Ile Tyr
290
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Met Ile Ile Val Arg Val Ile Gly Gly Leu Gly Asn Gln Met Phe Gln
1 5 10 15
Tyr Ala Leu Tyr Lys Ser Leu Glu Asn Glu Gly Lys Glu Val Lys Leu
20 25 30
Asp Leu Thr Gly Phe Gly Asp Tyr Asp Leu His Asn Gly Tyr Glu Leu
35 40 45
Asn Lys Ile Phe Asn Ile Asn Glu Asn Val Ala Thr Lys Asp Glu Ile
50 55 60
Asn Lys Leu Ile Lys Leu Pro Asp Asn Lys Val Leu Ser Met Ile Lys
65 70 75 80
Arg Lys Phe Phe Ser Ser Thr Ile Asn Tyr Tyr Ser Gln Asp Gln Phe
85 90 95
Lys Tyr Leu Ser Glu Ile Phe Gln Leu Asp Asn Val Tyr Leu Asp Gly
100 105 110
Tyr Trp Gln Ser Glu Lys Tyr Phe Gln Gly Ile Lys Glu Val Ile Arg
115 120 125
Lys Glu Phe Lys Phe Lys Gly Glu Pro Asn Pro Lys Asn Ile Glu Met
130 135 140
Val Lys Leu Met Arg Gly Ser Asn Ser Val Ser Ile His Phe Arg Arg
145 150 155 160
Gly Asp Tyr Ile Ser Asn Pro Asp Ala Tyr Lys Val His Gly Gly Ile
165 170 175
Thr Thr Ile His Tyr Tyr Glu Asn Ala Val Lys Glu Ile Lys Ser Lys
180 185 190
Val Lys Glu Pro Lys Phe Phe Ile Phe Ser Asp Asp Ile Lys Trp Val
195 200 205
Lys Glu Asn Phe Lys Leu Glu Asp Ala Phe Phe Ile Asp Trp Asn Thr
210 215 220
Gly Ser Glu Ser Tyr Arg Asp Ile Glu Leu Met Ser Asn Cys Lys His
225 230 235 240
Asn Ile Ile Ala Asn Ser Thr Phe Ser Trp Trp Gly Ala Trp Leu Asn
245 250 255
Lys Asn Lys Asn Lys Ile Val Ile Ala Pro Asn Gln Trp Phe Asn Thr
260 265 270
Ile Asp Thr Glu Asp Val Ile Pro Asp Thr Trp Gln Cys Ile Asn Thr
275 280 285
Phe
<210> 7
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<212> PRT
<213> Artificial Sequence
<220>
<223> alpha-1,2-fucosyltransferase
<400> 7
Met Asn Glu Ile His Val Leu Leu Thr Gly Arg Leu Gly Asn Gln Leu
1 5 10 15
Phe Gln Tyr Ala Phe Ala Arg Ser Leu Gln Lys Gln Tyr Gly Gly Arg
20 25 30
Ile Val Cys Asn Thr Phe Asp Leu Asp His Arg Ser Glu Lys Ser Lys
35 40 45
Val Ala Asp Gln Lys Phe Ser Tyr Ala Met Gly Asp Phe Lys Leu Asp
50 55 60
Glu Asn Val Ala Leu Glu Asp Ala Ala Leu Pro Trp Tyr Ala Asp Phe
65 70 75 80
Ser Ser Pro Leu Ile Lys Pro Val Lys Lys Leu Phe Pro Arg Arg Tyr
85 90 95
Phe Asp Phe Met Ala Arg Arg Gly Tyr Leu Met Trp Gln Arg Thr Asp
100 105 110
Tyr Met Pro Ile Pro Lys Leu Glu Cys Glu Asp Val Phe Ala Trp Gly
115 120 125
Trp Trp Gln Asp Ile Arg Tyr Phe Gln Asp Val Gln Thr Glu Leu Ser
130 135 140
Asp Glu Val Val Pro Val Thr Asp Pro Leu Pro Glu Asn Gln Tyr Ile
145 150 155 160
Tyr Asn Ala Ala Ser Gly Glu Glu Ser Val Cys Ile Ser Ile Arg Cys
165 170 175
Gly Asn Tyr Phe Asn Pro Thr Val Lys Lys Leu Leu Tyr Val Cys Thr
180 185 190
Pro Glu Tyr Phe Arg Asn Ala Val Glu Ser Ile Thr Lys Arg Leu Thr
195 200 205
His Pro Lys Phe Ile Val Phe Thr Asp Asp Val Asp Trp Val Lys Glu
210 215 220
Asn Ile Arg Phe Glu Ser Ala Tyr Pro Gln Tyr Glu Phe Leu Tyr Glu
225 230 235 240
Arg Gly Ser Asp Thr Val Glu Glu Lys Ile Arg Met Met Thr Leu Cys
245 250 255
Lys His Phe Ile Ile Ser Asn Ser Thr Phe Ser Trp Trp Ala Gln Phe
260 265 270
Leu Ser Lys Ser Glu Asn Lys Ile Val Ile Ala Pro Asp Arg Trp Phe
275 280 285
Val Asp Gly Arg Arg Ile Gly Leu Tyr Met His Gly Trp Thr Leu Ile
290 295 300
Pro Ala Gly Gln
305
<210> 8
<211> 317
<212> PRT
<213> Artificial Sequence
<220>
<223> alpha-1,2-fucosyltransferase
<400> 8
Met Ile Tyr Val Glu Met His Gly Arg Leu Gly Asn Gln Met Phe Gln
1 5 10 15
Tyr Ala Ala Ala Arg Ala Leu Gln Glu Lys Asn Asn Gln Pro Ile Met
20 25 30
Leu Ser Phe Arg Lys Val Ile Gly Ala Asn Thr Glu Gly Thr Ala Gly
35 40 45
Trp Glu Asn Ser Leu Lys Tyr Phe Asn Val Lys Pro Cys Glu Tyr Tyr
50 55 60
Met Gly Lys Lys Ser Leu Val Thr Glu Tyr Pro Val Glu Tyr Arg Leu
65 70 75 80
Leu Cys Tyr Ala Tyr Ala Leu Ser Tyr Lys Pro Leu Met Asn Asn Met
85 90 95
Asn Arg Trp Tyr Glu Tyr Gln Val Lys Cys Cys Arg Phe Leu Asp Arg
100 105 110
Phe Gly Ile Arg Trp Ile Ala Asn Gly Tyr Tyr Asp Phe His Tyr Asn
115 120 125
Gly Leu Lys Asn Tyr Leu Leu Asn Gly Ser Phe Glu Ser Pro Lys Tyr
130 135 140
Phe Asp Ser Ile Arg Asp Lys Leu Leu Glu Glu Phe Thr Pro Arg Glu
145 150 155 160
Glu Glu Arg Lys Glu Asn Lys Arg Leu Tyr Glu Gln Ile Arg Lys Arg
165 170 175
Asn Ser Val Cys Leu Ser Val Arg His Phe Gln Leu Thr Gly Lys Gln
180 185 190
Ala Asp Met Tyr Asp Val Cys Ser Leu Glu Tyr Tyr Gln Thr Ala Ile
195 200 205
Arg Lys Met Cys Glu Leu Ile Glu Asn Pro Leu Phe Val Val Phe Ser
210 215 220
Asp Asp Ile Glu Trp Val Lys Asn Thr Ile Asp Leu Ser Arg Val Glu
225 230 235 240
Val Val Tyr Glu Thr Pro Gly Asn Pro Val Trp Glu Lys Leu Arg Leu
245 250 255
Met Tyr Ser Cys Lys Asn Phe Ile Ile Pro Asn Ser Thr Phe Ala Trp
260 265 270
Trp Ala Gln Tyr Leu Ser Arg Asn Pro Asp Lys Tyr Val Leu Cys Pro
275 280 285
Ala Lys Trp Phe Asn Asn Asn Phe Glu Ser Pro Leu Ile Ala Ser Gln
290 295 300
Trp Val Arg Ile Asp Arg Glu Gly Asn Ile Val Asn Glu
305 310 315
<210> 9
<211> 289
<212> PRT
<213> Artificial Sequence
<220>
<223> alpha-1,2-fucosyltransferase
<400> 9
Met Lys Ile Val Lys Val Ile Gly Gly Leu Gly Asn Gln Met Phe Gln
1 5 10 15
Tyr Ala Phe Tyr Arg Asn Leu Lys Ala Lys Phe Gln Glu Val Lys Leu
20 25 30
Asp Ile Thr Ala Phe Glu Thr Tyr Lys Leu His Asn Gly Tyr Glu Leu
35 40 45
Glu Arg Val Phe Asp Ile Lys Pro Glu Tyr Ala Thr Lys Lys Glu Ile
50 55 60
Tyr Pro Leu Thr Thr Asn Arg Asn Ser Lys Ile Ser Lys Ile Lys Arg
65 70 75 80
Arg Ile Phe Gly Gly Lys Glu Thr Glu Tyr Ile Glu Lys Asp Leu Lys
85 90 95
Phe Asp Pro Glu Val Phe Lys Val Thr Gly Asp Val Tyr Phe Glu Gly
100 105 110
Tyr Trp Gln Thr Glu Lys Tyr Phe Lys Glu Ile Glu Asp Leu Ile Arg
115 120 125
Lys Asp Phe Gln Phe Lys Asn Pro Leu Thr Asn Lys Asn Leu Glu Leu
130 135 140
Ser Asn Lys Ile Lys Asn Glu Asn Ser Val Ser Ile His Val Arg Arg
145 150 155 160
Gly Asp Tyr Tyr Thr Ser Lys Lys Ala Glu Arg Lys His Gly Asn Ile
165 170 175
Ala Thr Ile Glu Tyr Tyr Gln Lys Ala Val Arg Lys Ile Thr Glu Phe
180 185 190
Val Asp Asn Pro Val Phe Tyr Ile Phe Ser Asp Asp Ile Pro Trp Val
195 200 205
Lys Glu Asn Leu Lys Leu Glu Asn Glu Val Ile Tyr Val Asp Trp Asn
210 215 220
Lys Gly Leu Asp Ser Tyr Ile Asp Met Gln Leu Met Ser Ile Cys Lys
225 230 235 240
His Asn Ile Ile Ala Asn Ser Thr Phe Ser Trp Trp Gly Ala Trp Leu
245 250 255
Asn Gln Asn Lys Asn Lys Ile Val Ile Ala Pro Ser Arg Trp Ile Asn
260 265 270
Asn Lys Arg Leu Asp Thr Ser Asp Val Ile Pro Lys Glu Trp Ile Lys
275 280 285
Ile
<210> 10
<211> 314
<212> PRT
<213> Artificial Sequence
<220>
<223> alpha-1,2-fucosyltransferase
<400> 10
Met Leu Tyr Val Glu Met Asp Gly Arg Cys Gly Asn Gln Leu Phe His
1 5 10 15
Tyr Ala Val Ala Arg Tyr Ile Gln Leu Ala Ile Gly Asn Lys Glu Lys
20 25 30
Leu Cys Leu Asn Phe Asn Lys Ile Phe Glu Lys Lys Asp Glu Asn Asn
35 40 45
Gly Trp Val Asp Tyr Leu Lys Asp Phe Lys Thr Val Pro Tyr Ser Tyr
50 55 60
Tyr Ser Lys Ser Gly Thr Ile Leu Lys Asn Glu Ser Asn Phe Ile Gln
65 70 75 80
Lys Ile Ala Ile Gly Leu Lys Ala Ile Gln Ile Lys Ser Leu Thr Lys
85 90 95
Lys Ser Arg Gln Glu Gln Ala Asp Lys Ala Glu Val Gly Gln Arg Thr
100 105 110
Leu Asn Lys Leu Gly Val Tyr Trp Val Arg Glu Gly Val Asn Gln Ile
115 120 125
Tyr Pro Tyr Lys Asn Asn Lys Ile Leu Val Ser Gly Ile Cys Glu Ser
130 135 140
Asn Phe Ile Tyr Glu Ile Gln Glu Gln Leu Gln Lys Glu Leu Ile Pro
145 150 155 160
Val Thr Pro Val Ser Ser Leu Asn Lys Ser Leu Leu Glu Lys Ile Asp
165 170 175
Asn Cys Asn Ser Val Cys Ile Ser Val Arg Arg Gly Asp Phe Phe Asn
180 185 190
Asn Lys Asn Ala Lys Lys Tyr Gly Val Cys Ser Pro Glu Tyr Tyr Ile
195 200 205
Arg Ala Lys Lys Tyr Phe Asp Lys Lys Arg Leu Glu Asn Thr Val Tyr
210 215 220
Phe Cys Phe Ser Asp Asp Ile Glu Trp Cys Lys Glu Asn Leu Lys Phe
225 230 235 240
Thr Asp Lys Asn Val Ile Phe Val Ser Gln Glu Met Pro Val Tyr Glu
245 250 255
Thr Leu Arg Leu Met Ser His Cys Lys His Phe Ile Leu Ser Asn Ser
260 265 270
Thr Phe Ser Trp Trp Gly Gln Phe Leu Ser Glu Tyr Lys Asp Lys Ile
275 280 285
Val Val Ser Pro Ala Arg Trp Asn Asn Asp Gly Tyr Asp Thr Asn Leu
290 295 300
Ile Asp Lys Asn Trp Ile Leu Ile Asp Ala
305 310
<210> 11
<211> 309
<212> PRT
<213> Artificial Sequence
<220>
<223> alpha-1,2-fucosyltransferase
<400> 11
Met Ile Tyr Val Glu Ile Arg Gly Asn Leu Gly Asn Gln Leu Phe Ile
1 5 10 15
Tyr Ala Thr Ala Lys Lys Ile Gln Lys Leu Thr Gly Gln Lys Ile Gln
20 25 30
Leu Asn Thr Thr Thr Leu Asn Lys Tyr Phe Pro Asn Tyr Lys Phe Gly
35 40 45
Leu Ser Glu Phe Ile Met Glu Asp Pro Asp Cys Phe Ile Glu Ser Tyr
50 55 60
Lys Lys Leu Pro Trp Phe Thr Asn Glu Tyr Leu Leu Pro Ile Lys Ile
65 70 75 80
Phe Lys Lys Ile Leu Asn Lys Thr Pro Lys Ile Asn Lys Ile Leu Ser
85 90 95
Asp Phe Phe Phe Lys Ala Phe Glu Lys Lys Gly Tyr Phe Ile Trp Arg
100 105 110
Gly Glu Thr Phe Lys Lys Phe Ser Leu Gly Asn His Lys Asn Tyr Tyr
115 120 125
Leu Ser Gly Phe Trp Gln Ser Glu Asp Tyr Phe Tyr Asp Ile Arg Asp
130 135 140
Glu Leu Leu Glu Ile Ile Thr Pro Ile Asn Ser Ile Arg Glu Cys Asn
145 150 155 160
Phe Glu Leu Leu Asn Leu Ile Arg Asn Ser Glu Ser Ile Cys Val Ser
165 170 175
Ile Arg Arg Gly Asp Tyr Val Asp Asn Pro Lys Ile Ser Ala Ile Tyr
180 185 190
Asn Val Cys Asp Ile Asn Tyr Phe Ile Glu Ser Val Asn Glu Ile Lys
195 200 205
Lys Asn Val Val Asn Val Lys Val Ile Cys Phe Ser Asp Asp Val Glu
210 215 220
Trp Val Lys Lys Asn Ile Lys Phe Asp Cys Glu Thr His Tyr Glu Thr
225 230 235 240
Tyr Gly Asn Ser Leu Ser Glu Lys Val Gln Leu Met Ser Ser Cys Lys
245 250 255
His Phe Val Leu Ser Asn Ser Ser Phe Ser Trp Trp Thr Glu Phe Leu
260 265 270
Ser Ile Arg Gly Gly Ile Thr Ile Ala Pro Lys Asn Trp Tyr Ala Asp
275 280 285
Glu Arg Glu Ala Asp Ile Tyr Arg Lys Asn Trp Ile Tyr Leu Glu Asp
290 295 300
Lys Thr Glu Glu Glu
305
<210> 12
<211> 306
<212> PRT
<213> Artificial Sequence
<220>
<223> alpha-1,2-fucosyltransferase
<400> 12
Met Glu Glu Ile His Thr Leu Leu Thr Gly Arg Leu Gly Asn Gln Leu
1 5 10 15
Phe Gln Tyr Ala Phe Ala Arg Asn Leu Gln Lys Gln Tyr Gly Gly Gln
20 25 30
Ile Tyr Cys Asp Val Tyr Glu Leu Glu His Arg Met Ser Lys Val Ala
35 40 45
Asp Glu Lys Phe Ser Tyr Ala Met Ser Gly Phe Lys Leu Asp Ala Gly
50 55 60
Val Ile Arg Glu Asp Gln Ala Phe Pro Trp Tyr Ala Asp Phe Ser Asn
65 70 75 80
Pro Val Ile Lys Pro Ile Lys Lys Ala Met Pro Arg Lys Tyr Phe Glu
85 90 95
Leu Met Ala Arg Arg Gly Tyr Leu Met Trp Gln Arg Ser Asp Tyr Met
100 105 110
Pro Ile Pro Val Leu Asp Thr Gln Arg Val Phe Ala Ser Gly Trp Trp
115 120 125
Gln Asp Ile Arg Tyr Leu Gln Asn Val Gln Glu Glu Leu Ser Asp Glu
130 135 140
Ile Val Pro Ile Thr Asn Pro Leu Gln Glu Asn Arg Tyr Ile Tyr Asp
145 150 155 160
Ala Ala His Asp Arg Asp Ser Val Cys Ile Ser Ile Arg Cys Gly Asn
165 170 175
Tyr Phe Asn Pro Thr Val Lys Lys Leu Leu Tyr Val Cys Asn Pro Gln
180 185 190
Tyr Phe His Asp Ser Val Lys Arg Ile Ser Gln Met Leu Ala His Pro
195 200 205
Lys Phe Ile Val Phe Thr Asp Asp Val Ser Trp Val Lys Glu His Leu
210 215 220
Lys Phe Glu Asp Thr Tyr Pro Gln Phe Glu Phe Leu Tyr Glu Arg Gly
225 230 235 240
Cys Asp Thr Ala Glu Glu Lys Ile Arg Met Met Ala Met Cys Asn Asn
245 250 255
Phe Ile Ile Ser Asn Ser Thr Phe Ser Trp Trp Ala Gln Phe Leu Ser
260 265 270
Lys Asn Lys Glu Lys Ile Val Ile Ala Pro Asp Lys Trp Phe Val Asp
275 280 285
Gly Arg Lys Ile Gly Leu Tyr Met Asp Gly Trp Thr Leu Val Pro Ala
290 295 300
Gly Arg
305
<210> 13
<211> 292
<212> PRT
<213> Artificial Sequence
<220>
<223> alpha-1,2-fucosyltransferase
<400> 13
Met Ile Ala Val Lys Ile Gly Asp Gly Met Gly Asn Gln Leu Phe Asn
1 5 10 15
Tyr Ala Cys Gly Tyr Ala Gln Ala Arg Arg Asp Gly Asp Ser Leu Val
20 25 30
Leu Asp Ile Ser Glu Cys Asp Asn Ser Thr Leu Arg Asp Phe Glu Leu
35 40 45
Asp Lys Phe His Leu Lys Tyr Asp Lys Lys Glu Ser Phe Pro Asn Arg
50 55 60
Asn Leu Gly Gln Lys Ile Tyr Lys Asn Leu Arg Arg Ala Leu Lys Tyr
65 70 75 80
His Val Ile Lys Glu Arg Glu Val Tyr His Asn Arg Asp His Arg Tyr
85 90 95
Asp Val Asn Asp Ile Asp Pro Arg Val Tyr Lys Lys Lys Gly Leu Arg
100 105 110
Asn Lys Tyr Leu Tyr Gly Tyr Trp Gln His Leu Ala Tyr Phe Glu Asp
115 120 125
Tyr Leu Asn Glu Ile Thr Ala Met Met Thr Pro Ala Tyr Glu Gln Ser
130 135 140
Glu Thr Val Lys Lys Leu Gln Glu Glu Phe Lys Lys Thr Pro Thr Cys
145 150 155 160
Ala Val His Val Arg Gly Gly Asp Ile Met Gly Pro Ala Gly Ala Tyr
165 170 175
Phe Lys His Ala Met Glu Arg Met Glu Gln Glu Lys Pro Gly Val Arg
180 185 190
Tyr Ile Val Phe Thr Asn Asp Met Glu Arg Ala Glu Glu Ala Leu Ala
195 200 205
Pro Val Leu Glu Ser Gln Lys Lys Asp Ala Val Gly Gln Ala Glu Asn
210 215 220
Arg Leu Glu Phe Val Ser Glu Met Gly Glu Phe Ser Asp Val Asp Glu
225 230 235 240
Phe Phe Leu Met Ala Ala Cys Gln Asn Gln Ile Leu Ser Asn Ser Thr
245 250 255
Phe Ser Thr Trp Ala Ala Tyr Leu Asn Gln Asn Pro Asp Lys Thr Val
260 265 270
Ile Met Pro Asp Asp Leu Leu Ser Glu Arg Met Arg Gln Lys Asn Trp
275 280 285
Ile Ile Leu Lys
290
<210> 14
<211> 293
<212> PRT
<213> Artificial Sequence
<220>
<223> alpha-1,2-fucosyltransferase
<400> 14
Met Ile Ile Val His Leu Cys Gly Gly Leu Gly Asn Gln Met Phe Gln
1 5 10 15
Tyr Ala Ala Gly Leu Ala Ala Ala His Arg Ile Gly Ser Glu Val Lys
20 25 30
Phe Asp Thr His Trp Phe Asp Ala Thr Cys Leu His Gln Gly Leu Glu
35 40 45
Leu Arg Arg Val Phe Gly Leu Glu Leu Pro Glu Pro Ser Ser Lys Asp
50 55 60
Leu Arg Lys Val Leu Gly Ala Cys Val His Pro Ala Val Arg Arg Leu
65 70 75 80
Leu Ala Gly His Phe Leu His Gly Leu Arg Pro Lys Ser Leu Val Ile
85 90 95
Gln Pro His Phe His Tyr Trp Thr Gly Phe Glu His Leu Pro Asp Asn
100 105 110
Val Tyr Leu Glu Gly Tyr Trp Gln Ser Glu Arg Tyr Phe Ser Asn Ile
115 120 125
Ala Asp Ile Ile Arg Gln Gln Phe Arg Phe Val Glu Pro Leu Asp Pro
130 135 140
His Asn Ala Ala Leu Met Asp Glu Met Gln Ser Gly Val Ser Val Ser
145 150 155 160
Leu His Ile Arg Arg Gly Asp Tyr Phe Asn Asn Pro Gln Met Arg Arg
165 170 175
Val His Gly Val Asp Leu Ser Glu Tyr Tyr Pro Ala Ala Val Ala Thr
180 185 190
Met Ile Glu Lys Thr Asn Ala Glu Arg Phe Tyr Val Phe Ser Asp Asp
195 200 205
Pro Gln Trp Val Leu Glu His Leu Lys Leu Pro Val Ser Tyr Thr Val
210 215 220
Val Asp His Asn Arg Gly Ala Ala Ser Tyr Arg Asp Met Gln Leu Met
225 230 235 240
Ser Ala Cys Arg His His Ile Ile Ala Asn Ser Thr Phe Ser Trp Trp
245 250 255
Gly Ala Trp Leu Asn Pro Arg Pro Asp Lys Val Val Ile Ala Pro Arg
260 265 270
His Trp Phe Asn Val Asp Val Phe Asp Thr Arg Asp Leu Tyr Cys Pro
275 280 285
Gly Trp Ile Val Leu
290
<210> 15
<211> 300
<212> PRT
<213> Artificial Sequence
<220>
<223> alpha-1,2-fucosyltransferase
<400> 15
Met Ala Phe Lys Val Val Gln Ile Cys Gly Gly Leu Gly Asn Gln Met
1 5 10 15
Phe Gln Tyr Ala Phe Ala Lys Ser Leu Gln Lys His Ser Asn Thr Pro
20 25 30
Val Leu Leu Asp Ile Thr Ser Phe Asp Trp Ser Asp Arg Lys Met Gln
35 40 45
Leu Glu Leu Phe Pro Ile Asp Leu Pro Tyr Ala Ser Ala Lys Glu Ile
50 55 60
Ala Ile Ala Lys Met Gln His Leu Pro Lys Leu Val Arg Asp Ala Leu
65 70 75 80
Lys Cys Met Gly Phe Asp Arg Val Ser Gln Glu Ile Val Phe Glu Tyr
85 90 95
Glu Pro Lys Leu Leu Lys Pro Ser Arg Leu Thr Tyr Phe Phe Gly Tyr
100 105 110
Phe Gln Asp Pro Arg Tyr Phe Asp Ala Ile Ser Pro Leu Ile Lys Gln
115 120 125
Thr Phe Thr Leu Pro Pro Pro Pro Glu Asn Asn Lys Asn Asn Asn Lys
130 135 140
Lys Glu Glu Glu Tyr Gln Cys Lys Leu Ser Leu Ile Leu Ala Ala Lys
145 150 155 160
Asn Ser Val Phe Val His Ile Arg Arg Gly Asp Tyr Val Gly Ile Gly
165 170 175
Cys Gln Leu Gly Ile Asp Tyr Gln Lys Lys Ala Leu Glu Tyr Met Ala
180 185 190
Lys Arg Val Pro Asn Met Glu Leu Phe Val Phe Cys Glu Asp Leu Glu
195 200 205
Phe Thr Gln Asn Leu Asp Leu Gly Tyr Pro Phe Met Asp Met Thr Thr
210 215 220
Arg Asp Lys Glu Glu Glu Ala Tyr Trp Asp Met Leu Leu Met Gln Ser
225 230 235 240
Cys Gln His Gly Ile Ile Ala Asn Ser Thr Tyr Ser Trp Trp Ala Ala
245 250 255
Tyr Leu Ile Glu Asn Pro Glu Lys Ile Ile Ile Gly Pro Lys His Trp
260 265 270
Leu Phe Gly His Glu Asn Ile Leu Cys Lys Glu Trp Val Lys Ile Glu
275 280 285
Ser His Phe Glu Val Lys Ser Gln Lys Tyr Asn Ala
290 295 300
<210> 16
<211> 327
<212> PRT
<213> Artificial Sequence
<220>
<223> alpha-1,2-fucosyltransferase
<400> 16
Met Ala Gly His Ser Cys Gly Lys Tyr Ala Asn Ser Trp Arg Lys Tyr
1 5 10 15
Ala Gly Ile Ser Arg Phe Asn Pro Phe Pro Cys Leu Asn Met Ala Lys
20 25 30
Gly Lys Ile Ile Val Met Arg Leu Phe Gly Gly Leu Gly Asn Gln Leu
35 40 45
Phe Gln Tyr Ala Phe Leu Phe Ala Leu Ser Arg Gln Gly Gly Lys Ala
50 55 60
Arg Leu Glu Thr Ser Ser Tyr Glu His Asp Asp Lys Arg Val Cys Glu
65 70 75 80
Leu His His Phe Arg Val Ser Leu Pro Ile Glu Gly Gly Pro Pro Pro
85 90 95
Trp Ala Phe Arg Lys Ser Arg Ile Pro Ala Cys Leu Arg Ser Leu Phe
100 105 110
Ala Ala Pro Lys Tyr Pro His Phe Arg Glu Glu Lys Arg His Gly Phe
115 120 125
Asp Pro Gly Leu Ala Ala Pro Pro Arg Arg His Thr Tyr Phe Lys Gly
130 135 140
Tyr Phe Gln Thr Glu Gln Tyr Phe Leu His Cys Arg Glu Gln Leu Cys
145 150 155 160
Arg Glu Phe Arg Leu Lys Thr Pro Leu Thr Pro Glu Asn Ala Arg Ile
165 170 175
Leu Glu Asp Ile Arg Ser Cys Cys Ser Ile Ser Leu His Ile Arg Arg
180 185 190
Thr Asp Tyr Leu Ser Asn Pro Tyr Leu Ser Pro Pro Pro Leu Glu Tyr
195 200 205
Tyr Leu Arg Ser Met Ala Glu Met Glu Gly Arg Leu Arg Ala Ala Gly
210 215 220
Ala Pro Gln Glu Ser Leu Arg Tyr Phe Ile Phe Ser Asp Asp Ile Glu
225 230 235 240
Trp Ala Arg Gln Asn Leu Arg Pro Ala Leu Pro His Val His Val Asp
245 250 255
Ile Asn Asp Gly Gly Thr Gly Tyr Phe Asp Leu Glu Leu Met Arg Asn
260 265 270
Cys Arg His His Ile Ile Ala Asn Ser Thr Phe Ser Trp Trp Ala Ala
275 280 285
Trp Leu Asn Glu His Ala Glu Lys Ile Val Ile Ala Pro Arg Ile Trp
290 295 300
Phe Asn Arg Glu Glu Gly Asp Arg Tyr His Thr Asp Asp Ala Leu Ile
305 310 315 320
Pro Gly Ser Trp Leu Arg Ile
325
Claims (24)
- 락토오스를 포함하는 배지에서 알파-1,2-푸코오스 전이효소(alpha-1,2-fucosyltransferase)를 가지는 미생물을 배양하여, 락토오스로부터 2’-푸코실락토오스를 생산하는 단계; 및
락토오스 가수분해효소를 처리하는 단계를 포함하는, 2’-푸코실락토오스의 제조 방법. - 제1항에 있어서, 상기 락토오스 가수분해효소를 처리하는 단계는, 상기 미생물을 포함하는 배양액에서 수행되거나, 또는 상기 미생물 균체가 제거된 배양액에서 수행되는 것인, 방법.
- 제1항에 있어서, 상기 락토오스 가수분해효소는 상기 미생물을 포함하는 배양액에 처리되며, 상기 배양액에 락토오스 가수분해효소를 처리하여 배양을 지속하는 단계 추가로 포함하는, 방법.
- 제2항에 있어서, 상기 락토오스 가수분해효소를 처리하는 단계를, 상기 미생물을 포함하는 배양액에서 수행하는 경우, 2’-푸코실락토오스 함량의 증가율이 10% 이하일 때 첨가되는 것인, 방법.
- 제2항에 있어서, 상기 락토오스 가수분해효소를 처리하는 단계를, 상기 미생물을 포함하는 배양액에서 수행하는 경우, 배양액 내 2’-푸코실락토오스 함량의 최댓값을 도달한 시점 이후에 첨가되는 것인, 방법.
- 제2항에 있어서, 상기 락토오스 가수분해효소를 처리하는 단계를, 상기 미생물을 포함하는 배양액에서 수행하는 경우, 2’-푸코실락토오스 전환반응이 정상상태일 때 첨가되는 것인, 방법.
- 제1항에 있어서, 상기 락토오스 가수분해효소 처리 후 배양액은, 처리 전 배양액의 락토오스 함량 100중량%을 기준으로, 락토오스 함량이 5중량% 이하인, 방법.
- 제1항 내지 제7항 중 어느 한 항에 있어서, 상기 미생물의 배양액에서 균체를 제거하여 상등액을 얻는 단계를 추가로 포함하는, 방법.
- 제8항에 있어서, 상기 상등액을 정제하여 2’-푸코실락토오스를 얻는 단계를 추가로 포함하는, 방법.
- 제9항에 있어서, 정제는 활성탄 처리, 초미세여과 (Ultrafiltration), 나노여과 (Nanofiltration), 전기투석 (Electrodialysis), 및 이온교환수지 (Ion exchange)로 이루어지는 군에서 선택된 1종 이상의 공정을 포함하는 것인, 방법.
- 제10항에 있어서, 상기 활성탄 처리는 정제공정 중 처음에 수행되거나, 상기 초미세여과는 상기 나노여과 이전에 수행되거나, 상기 나노여과는 상기 전기투석 이전에 수행되거나, 또는 상기 이온교환수지는 정제공정 중 마지막에 수행되는 것인, 방법.
- 제10항에 있어서, 상기 정제는 활성탄 처리, 초미세여과, 나노여과, 전기투석, 및 이온교환수지 순서로 수행되는 것인, 방법.
- 제9에 있어서, 상기 방법은 순도 45중량% 이상의 2’-푸코실락토오스를 얻는 것인, 방법.
- 제9항에 있어서, 당류 고형분 100중량% 기준으로 2’-푸코실락토오스 함량이 45중량% 이상인 정제물을 얻는 것인, 방법.
- 제8항에 있어서, 상기 상등액을 농축 또는 분무건조하여 2’-푸코실락토오스 분말을 얻는 단계를 추가로 포함하는, 방법.
- 제8항에 있어서, 상기 상등액을 정제하는 단계;
상기 정제된 상등액을 농축하는 단계; 및
상기 농축된 상등액을 분무건조하여 2’-푸코실락토오스 분말을 얻는 단계를 추가로 포함하는, 방법. - 제1항에 있어서, 상기 미생물은 탄소원으로 포도당 및 갈락토오스로 이루어지는 군에서 선택된 1종 이상을 사용 가능한 것인, 방법.
- 제1항에 있어서, 상기 미생물은 LacZ 유전자가 결실된 것인, 방법.
- 제1항에 있어서, 상기 미생물은 푸코오스 합성 유전자를 발현하는 것인, 방법.
- 제19항에 있어서, 상기 푸코오스 합성 유전자는 GDP-D-만노오스-4,6-데하이드라타아제 (GDP-D-mannose-4,6-dehydratase), GDP-L-푸코오스 신타아제 (GDP-L-fucose synthase), 포스포만노뮤타아제 (phosphomannomurase), 및 GTP 만노오스-1-포스페이트 구아닐릴트랜스퍼라아제 (GTP-mannose-1-phosphate guanylyltransferase)로 이루어지는 군에서 선택된 1종 이상인, 방법.
- 제1항에 있어서, 상기 미생물은 락토오스 막 수송 단백질을 발현하는 것인, 방법.
- 제21항에 있어서, 상기 락토오스 막 수송 단백질은 Lac12 및 LacY로 이루어지는 군에서 선택된 1종 이상인, 방법
- 제1항에 있어서, 상기 미생물은 바실러스 속 (Bacillus sp.) 미생물, 코리네박테리움 속 (Corynebacterium sp.) 미생물, 대장균 속 (Escherichia sp.) 미생물, 및 효모 (yeast)로 이루어지는 군에서 선택된 1종 이상인, 방법.
- 제23항에 있어서, 상기 바실러스 속 (Bacillus sp.) 미생물은 바실러스 메가테리움 (Bacillus megaterium), 바실러스 서브틸리스 (Bacillus subtilis), 바실러스 세레우스 (Bacillus cereus), 바실러스 코아귤런스 (Bacillus coagulans), 바실러스 리체니포르미스 (Bacillus licheniformis), 및 바실러스 스테아로테르모필루스 (Bacillus stearothermophilus)로 이루어지는 군에서 선택된 1종 이상,
상기 코리네박테리움 속 (Corynebacterium sp.) 미생물은 코리네박테리움 글루타미쿰 (Corynebacterium glutatamicum),
상기 대장균 속 (Escherichia sp.) 미생물은 대장균 (Escherichia coli), 또는
상기 효모 (yeast)는 사카로미세스 세레비시아 (Saccharomyces cerevisiae), 및 캔디다 유틸리스 (Candida utilis)로 이루어지는 군에서 선택된 1종 이상인, 방법.
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