CA2853677C - Methods and materials for enzymatic synthesis of mogroside compounds - Google Patents

Methods and materials for enzymatic synthesis of mogroside compounds Download PDF

Info

Publication number
CA2853677C
CA2853677C CA2853677A CA2853677A CA2853677C CA 2853677 C CA2853677 C CA 2853677C CA 2853677 A CA2853677 A CA 2853677A CA 2853677 A CA2853677 A CA 2853677A CA 2853677 C CA2853677 C CA 2853677C
Authority
CA
Canada
Prior art keywords
polypeptide
mogroside
amino acid
seq
sequence identity
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CA2853677A
Other languages
English (en)
French (fr)
Other versions
CA2853677A1 (en
Inventor
Yaoquan Liu
Jung Yeop Lee
Monika KHARE
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evolva Holding SA
Original Assignee
Evolva AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Evolva AG filed Critical Evolva AG
Publication of CA2853677A1 publication Critical patent/CA2853677A1/en
Application granted granted Critical
Publication of CA2853677C publication Critical patent/CA2853677C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P33/00Preparation of steroids
    • C12P33/20Preparation of steroids containing heterocyclic rings
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00Preparation of compounds containing saccharide radicals
    • C12P19/18Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P33/00Preparation of steroids

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Enzymes And Modification Thereof (AREA)
CA2853677A 2011-11-23 2012-11-19 Methods and materials for enzymatic synthesis of mogroside compounds Active CA2853677C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161563303P 2011-11-23 2011-11-23
US61/563,303 2011-11-23
PCT/IB2012/002857 WO2013076577A1 (en) 2011-11-23 2012-11-19 Methods and materials for enzymatic synthesis of mogroside compounds

Publications (2)

Publication Number Publication Date
CA2853677A1 CA2853677A1 (en) 2013-05-30
CA2853677C true CA2853677C (en) 2019-01-29

Family

ID=47624376

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2853677A Active CA2853677C (en) 2011-11-23 2012-11-19 Methods and materials for enzymatic synthesis of mogroside compounds

Country Status (14)

Country Link
US (2) US9920349B2 (enExample)
EP (1) EP2783009B1 (enExample)
JP (1) JP6084983B2 (enExample)
KR (1) KR101791597B1 (enExample)
CN (1) CN103958693B (enExample)
AU (2) AU2012342114B2 (enExample)
BR (1) BR112014012543A2 (enExample)
CA (1) CA2853677C (enExample)
IN (1) IN2014CN03557A (enExample)
MX (1) MX342851B (enExample)
MY (1) MY170686A (enExample)
RU (1) RU2633644C2 (enExample)
SG (1) SG11201401927PA (enExample)
WO (1) WO2013076577A1 (enExample)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6177127B2 (ja) 2010-06-02 2017-08-09 エボルバ, インク.Evolva, Inc. ステビオールグリコシドの組換え生成
SG10201606567TA (en) 2011-08-08 2016-10-28 Evolva Sa Recombinant production of steviol glycosides
RU2633644C2 (ru) 2011-11-23 2017-10-16 Эвольва Са Способы ферментативного синтеза могрозидных соединений
TW201402599A (zh) * 2012-05-30 2014-01-16 Suntory Holdings Ltd 甜菊糖苷糖苷轉化酵素及編碼該酵素之基因
SG10201704575XA (en) 2012-12-04 2017-07-28 Evolva Sa Methods and materials for biosynthesis of mogroside compounds
US10017804B2 (en) 2013-02-11 2018-07-10 Evolva Sa Efficient production of steviol glycosides in recombinant hosts
EP3179869A1 (en) 2014-08-11 2017-06-21 Evolva SA Production of steviol glycosides in recombinant hosts
BR112017004712B1 (pt) 2014-09-09 2021-11-03 Evolva Sa Hospedeiro recombinante que produz um precursor de glicosídeo de esteviol, métodos para produzir um precursor de glicosídeo de esteviol, um esteviol ou um ou mais glicosídeos de esteviol, cultura do dito hospedeiro e lisado da cultura do dito hospedeiro
US20170283844A1 (en) 2014-09-11 2017-10-05 The State of Israel, Ministry of Agriculture & Rural Development, Argricultural Research Organiza Methods of producing mogrosides and compositions comprising same and uses thereof
EP3201315A2 (en) 2014-10-01 2017-08-09 Evolva SA Methods and materials for biosynthesis of mogroside compounds
EP3208342A4 (en) 2014-10-17 2018-07-04 Suntory Holdings Limited Mogrol glycosyltransferase and gene encoding same
US10626430B2 (en) 2015-01-20 2020-04-21 Suntory Holdings Limited Method for preparing mogroside having no β-1,6-glucoside bond
BR112017016338A2 (pt) 2015-01-30 2018-03-27 Evolva Sa produção de glicosídeos de esteviol em hospedeiros recombinantes
CN107567492B (zh) 2015-03-16 2022-10-14 帝斯曼知识产权资产管理有限公司 Udp-糖基转移酶
WO2017025362A1 (en) 2015-08-07 2017-02-16 Evolva Sa Production of steviol glycosides in recombinant hosts
ES2925017T3 (es) 2015-10-29 2022-10-13 Firmenich Incorporated Edulcorantes de alta intensidad
CN106924274B (zh) * 2015-12-29 2019-01-04 成都普睿法药物研发有限公司 葫芦烷型四环三萜类化合物抗肺纤维化应用
MY198001A (en) 2016-04-13 2023-07-25 Evolva SA Production of steviol glycoside in recombinant hosts
US10815514B2 (en) 2016-05-16 2020-10-27 Evolva Sa Production of steviol glycosides in recombinant hosts
BR112018073662A2 (pt) * 2016-05-16 2019-02-19 Evolva Sa produção de glicosídeos de esteviol em hospedeiros recombinantes
CN109477126B (zh) 2016-07-19 2023-06-20 三得利控股株式会社 罗汉果醇或罗汉果醇糖苷的生产方法
EP3535406A1 (en) 2016-11-07 2019-09-11 Evolva SA Production of steviol glycosides in recombinant hosts
US11060124B2 (en) * 2017-05-03 2021-07-13 Firmenich Incorporated Methods for making high intensity sweeteners
CN111246749A (zh) 2017-05-19 2020-06-05 可口可乐公司 翅子罗汉果i甜味化的组合物及其用途
CN116941752A (zh) 2017-06-02 2023-10-27 奇华顿股份有限公司 组合物
WO2018229283A1 (en) 2017-06-15 2018-12-20 Evolva Sa Production of mogroside compounds in recombinant hosts
CN107189976B (zh) * 2017-07-28 2022-03-11 李华政 促进罗汉果ugt72b21基因表达的方法
CA3118467A1 (en) 2018-11-07 2020-05-14 Firmenich Incorporated Methods for making high intensity sweeteners
JP2022512931A (ja) 2018-11-07 2022-02-07 フィルメニッヒ インコーポレイテッド 高甘味度甘味料の製造方法
CN113302298B (zh) 2018-11-09 2025-02-25 银杏生物制品公司 罗汉果甙的生物合成
CN110669094B (zh) * 2019-10-14 2021-12-21 上海交通大学 罗汉果新苷及其制备方法
KR102362135B1 (ko) * 2019-10-25 2022-02-14 고려대학교 산학협력단 테르펜 당쇄 부가 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 조성물
WO2021188703A1 (en) * 2020-03-17 2021-09-23 The Coca-Cola Company Novel mogroside production system and methods
EP4138574A1 (en) 2020-04-20 2023-03-01 Givaudan SA Compositions
GB202007984D0 (en) 2020-05-28 2020-07-15 Givaudan Sa Compositions
CN112063647B (zh) * 2020-09-17 2023-05-02 云南农业大学 酿酒酵母重组菌Cuol01的构建方法、酿酒酵母重组菌Cuol02及应用
CN116064712B (zh) * 2022-10-08 2025-05-06 中国药科大学 一种罗汉果醇的生物合成方法
WO2024218244A1 (en) 2023-04-20 2024-10-24 Dsm Ip Assets B.V. Strains and methods for the production of mogrosides

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6399321B1 (en) * 1999-08-18 2002-06-04 National Research Council Of Canada Methods for screening UDP-glucose:glycoprotein glucosyltransferase (UGGT) activity and nucleic acid encoding for UGGT
EP1510573A1 (en) * 2003-09-01 2005-03-02 Austria Wirtschaftsservice Gesellschaft mit beschränkter Haftung Method for detoxification of mycotoxins
US20080148432A1 (en) * 2005-12-21 2008-06-19 Mark Scott Abad Transgenic plants with enhanced agronomic traits
EP2194140A2 (en) 2005-03-02 2010-06-09 Metanomics GmbH Process for the production of fine chemicals
US8257948B1 (en) * 2011-02-17 2012-09-04 Purecircle Usa Method of preparing alpha-glucosyl Stevia composition
US8956677B2 (en) 2005-11-23 2015-02-17 The Coca-Cola Company High-potency sweetener composition with glucosamine and compositions sweetened therewith
RU2008123259A (ru) * 2005-11-23 2009-12-27 Дзе Кока-Кола Компани (US) Композиция интенсивного подсластителя с противовоспалительным средством и подслащенные ею композиции
US7927851B2 (en) 2006-03-21 2011-04-19 Vineland Research And Innovation Centre Compositions having ent-kaurenoic acid 13-hydroxylase activity and methods for producing same
WO2008062165A2 (en) * 2006-11-22 2008-05-29 The University Of York Monoterpenoid modifying enzymes
WO2008065370A2 (en) * 2006-12-01 2008-06-05 The University Of York Sesquiterpenoid modifying enzymes
GB0904639D0 (en) * 2009-03-18 2009-04-29 Univ York Assay
JP6177127B2 (ja) 2010-06-02 2017-08-09 エボルバ, インク.Evolva, Inc. ステビオールグリコシドの組換え生成
RU2633644C2 (ru) 2011-11-23 2017-10-16 Эвольва Са Способы ферментативного синтеза могрозидных соединений
SG10201704575XA (en) 2012-12-04 2017-07-28 Evolva Sa Methods and materials for biosynthesis of mogroside compounds

Also Published As

Publication number Publication date
MX2014006276A (es) 2014-10-13
AU2017235907A1 (en) 2017-10-12
KR101791597B1 (ko) 2017-10-30
EP2783009A1 (en) 2014-10-01
HK1200494A1 (zh) 2015-08-07
RU2633644C2 (ru) 2017-10-16
US10738340B2 (en) 2020-08-11
BR112014012543A2 (pt) 2017-06-13
AU2012342114A1 (en) 2014-05-22
JP2014533518A (ja) 2014-12-15
JP6084983B2 (ja) 2017-02-22
US20140308698A1 (en) 2014-10-16
WO2013076577A1 (en) 2013-05-30
RU2014125216A (ru) 2015-12-27
KR20140099281A (ko) 2014-08-11
SG11201401927PA (en) 2014-09-26
CA2853677A1 (en) 2013-05-30
MX342851B (es) 2016-10-14
US9920349B2 (en) 2018-03-20
EP2783009B1 (en) 2016-04-13
CN103958693B (zh) 2016-08-24
IN2014CN03557A (enExample) 2015-10-09
CN103958693A (zh) 2014-07-30
US20180237819A1 (en) 2018-08-23
MY170686A (en) 2019-08-26
AU2012342114B2 (en) 2017-12-21

Similar Documents

Publication Publication Date Title
CA2853677C (en) Methods and materials for enzymatic synthesis of mogroside compounds
Shibuya et al. Identification and characterization of glycosyltransferases involved in the biosynthesis of soyasaponin I in Glycine max
AU2022204430A1 (en) Methods and materials for biosynthesis of mogroside compounds
US20250331481A1 (en) Group of udp-glycosyltransferase for catalyzing carbohydrate chain elongation, and application thereof
US20160215306A1 (en) Method for producing modified resveratrol
AU2018220068A1 (en) Methods for improved production of rebaudioside D and rebaudioside M
Irmisch et al. Complete biosynthesis of the anti-diabetic plant metabolite montbretin A
Lyu et al. Identification and characterization of three flavonoid 3-O-glycosyltransferases from Epimedium koreanum Nakai
JP7305213B2 (ja) 変異体酵素を介するステビオール配糖体レバウシオシドiの生合成的産生
CN104357418A (zh) 一种糖基转移酶及其突变体在合成人参皂苷Rh2中的应用
CN106350565A (zh) 一种稀有人参皂苷Rh2的生产方法
CN105087739A (zh) 一种新的制备稀有人参皂苷的催化体系及其应用
Zhang et al. Identification of the key residues of the uridine diphosphate glycosyltransferase 91D2 and its effect on the accumulation of steviol glycosides in Stevia rebaudiana
WO2021164673A1 (zh) 双功能碳苷糖基转移酶及其应用
Overwin et al. Flavanone and isoflavone glucosylation by non-Leloir glycosyltransferases
Yang et al. Systems metabolic engineering of Escherichia coli to enhance the production of flavonoid glucuronides
WO2023030065A1 (zh) 一种糖基转移酶及其应用
Malik et al. Structural, functional, and mutagenesis studies of UDP-glycosyltransferases
HK1200494B (en) Methods and materials for enzymatic synthesis of mogroside compounds
Nidetzky Glycosyltransferase cascades made fit for the biocatalytic production of natural product glycosides
Xu et al. Convergent Evolution and De Novo Reconstitution of Apiin Biosynthesis
Masada et al. Production of unnatural bioactive glycosides using plant secondary product glycosyltransferases
Masada et al. Full Text HTML

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20160825