Biocatalytic Fluoroalkylation Using Fluorinated S-Adenosyl-l-methionine Cofactors

被引：9

作者：

Ding, Wenping ^{[1
,2
]}

Zhou, Minqi ^{[3
]}

Li, Huayu ^{[4
]}

Li, Miao ^{[4
]}

Qiu, Yanping ^{[4
]}

Yin, Yu ^{[5
]}

Pan, Lifeng ^{[4
]}

Yang, Wenchao ^{[1
]}

Du, Yanan ^{[4
]}

Zhang, Xingang ^{[3
]}

Tang, Zhijun ^{[4
]}

Liu, Wen ^{[1
,4
]}

机构：

[1] Cent China Normal Univ, Coll Chem, Int Joint Res Ctr Intelligent Biosensor Technol &, Key Lab Pesticide & Chem Biol,Minist Educ, Wuhan 430079, Peoples R China

[2] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

[3] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[4] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

[5] Shanghai Jiao Tong Univ, Sch Pharm, Shanghai 200240, Peoples R China

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 30期

基金：

中国国家自然科学基金;

关键词：

TRIFLUOROMETHYLATION; BIOSYNTHESIS; GLYCOPEPTIDE; GENERATION; PRODUCT; ANALOGS; TOOL;

D O I：

10.1021/acs.orglett.3c02028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Modification of organic molecules with fluorine functionalitiesoffers a critical approach to develop new pharmaceuticals. Here, wereport a multienzyme strategy for biocatalytic fluoroalkylation using S-adenosyl-l-methionine (SAM)-dependent methyltransferases(MTs) and fluorinated SAM cofactors prepared from ATP and fluorinated l-methionine analogues by an engineered human methionine adenosyltransferasehMAT2A(I322A). This work introduces the first example ofbiocatalytic 3,3-difluoroallylation. Importantly, this strategy canbe applied to late-stage site-selective fluoroalkylation of complexmolecule vancomycin with conversions up to 99%.

引用

页码：5650 / 5655

页数：6

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