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1. WO2020107781 - METHOD FOR PREPARING (S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-FORMIC ACID BY ENZYMATIC RESOLUTION

Publication Number WO/2020/107781
Publication Date 04.06.2020
International Application No. PCT/CN2019/083877
International Filing Date 23.04.2019
IPC
C12P 41/00 2006.01
CCHEMISTRY; METALLURGY
12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
41Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
CPC
C12P 17/12
CCHEMISTRY; METALLURGY
12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
17Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
10Nitrogen as only ring hetero atom
12containing a six-membered hetero ring
C12P 41/00
CCHEMISTRY; METALLURGY
12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
41Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
Applicants
  • 苏州同力生物医药有限公司 TONGLI BIOMEDICAL CO., LTD. [CN]/[CN]
  • 浙江大学 ZHEJIANG UNIVERSITY [CN]/[CN]
Inventors
  • 吴坚平 WU, Jianping
  • 居述云 JU, Shuyun
  • 施俊巍 SHI, Junwei
  • 杨立荣 YANG, Lirong
  • 钱明心 QIAN, Mingxin
Agents
  • 苏州创元专利商标事务所有限公司 SUZHOU CREATOR PATENT & TRADEMARK AGENCY LTD.
Priority Data
201811454845.230.11.2018CN
Publication Language Chinese (ZH)
Filing Language Chinese (ZH)
Designated States
Title
(EN) METHOD FOR PREPARING (S)-1,2,3,4-TETRAHYDROISOQUINOLINE-3-FORMIC ACID BY ENZYMATIC RESOLUTION
(FR) PROCÉDÉ DE PRÉPARATION D’ACIDE (S)-1,2,3,4-TÉTRAHYDROISOQUINOLÉINE-3-FORMIQUE PAR RÉSOLUTION ENZYMATIQUE
(ZH) 一种酶法拆分制备(S)-1,2,3,4-四氢异喹啉-3-甲酸的方法
Abstract
(EN)
Disclosed is a novel method for preparing (S)-1,2,3,4-tetrahydroisoquinoline-3-formic acid by enzymatic resolution. Said method comprises: using racemic 1,2,3,4-tetrahydroisoquinoline-3-formic acid or a salt thereof as a substrate, using an in vitro D-amino acid oxidase or a cell expressing a D-amino acid oxidase intracellularly as a catalyst to selectively catalyze the oxidative dehydrogenation reaction of (R)-1,2,3,4-tetrahydroisoquinoline-3-formic acid, and (S)-1,2,3,4-tetrahydroisoquinoline-3-formic acid being not catalyzed and retained in the reaction system, thereby preparing and obtaining (S)-1,2,3,4-tetrahydroisoquinoline-3-formic acid. The (S)-1,2,3,4-tetrahydroisoquinoline-3-formic acid is a key intermediate of the antihypertensive drug Quinapril. The present invention has a reaction yield greater than 49% and an e.e. value up to 99%, and has the features of mild reaction conditions, high stereoselectivity and reaction efficiency, and a relatively simple process.
(FR)
Nouveau procédé de préparation d'acide (S)-1,2,3,4-tétrahydroisoquinoléine-3-formique par résolution enzymatique. Ledit procédé comprend : l'utilisation d'acide 1,2,3,4-tétrahydroisoquinoline-3-formique racémique ou d'un sel correspondant en tant que substrat, à l'aide d'une D aminoacide oxydase In vitro ou d'une cellule exprimant une D aminoacide oxydase intracellulaire en tant que catalyseur pour catalyser de manière sélective la réaction de déshydrogénation oxydative d'acide (R)-1,2,3,4-tétrahydroisoquinoléine-3-formique, et l'acide (S)-1,2,3,4-tétrahydroisoquinoléine-3-formique n'étant pas catalysé et étant retenu dans le système de réaction, ce qui permet de préparer et d'obtenir de l'acide (S)-1,2,3,4-tétrahydroisoquinoléine-3-formique. L'acide (S)-1,2,3,4-tétrahydroisoquinoléine-3-formique est un intermédiaire clé du médicament antihypertenseur Quinapril. La présente invention a un rendement de réaction supérieur à 49 % et une valeur e.e. allant jusqu'à 99 %, et a les caractéristiques de conditions de réaction douces, de stéréosélectivité et d'efficacité de réaction élevées, et un consiste en un procédé relativement simple.
(ZH)
本发明公开了一种酶法拆分制备(S)-1,2,3,4-四氢异喹啉-3-甲酸的新方法,所述方法为:以外消旋1,2,3,4-四氢异喹啉-3-甲酸或其盐为底物,利用离体的D-氨基酸氧化酶或胞内表达D-氨基酸氧化酶的细胞作为催化剂,选择性催化(R)-1,2,3,4-四氢异喹啉-3-甲酸进行氧化脱氢反应,(S)-1,2,3,4-四氢异喹啉-3-甲酸未被催化,保留在反应体系中,由此制备获得(S)-1,2,3,4-四氢异喹啉-3-甲酸。所述(S)-1,2,3,4-四氢异喹啉-3-甲酸是降压药喹那普利的关键中间体。本发明反应收率>49%,ee值达99%,具有反应条件温和、立体选择性强、反应效率高、工艺相对简单等特点。
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