Carboxylic acid reductases enable intramolecular lactamization reactions

被引:14
作者
Qin, Zongmin [1 ,2 ]
Zhang, Xiaohui [2 ]
Sang, Xianke [2 ]
Zhang, Wuyuan [1 ,2 ,3 ]
Qu, Ge [1 ,2 ,3 ]
Sun, Zhoutong [1 ,2 ,3 ]
机构
[1] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[2] Chinese Acad Sci, Tianjin Inst Ind Biotechnol, Tianjin 300308, Peoples R China
[3] Natl Technol Innovat Ctr Synthet Biol, Tianjin 300308, Peoples R China
来源
GREEN SYNTHESIS AND CATALYSIS | 2022年 / 3卷 / 03期
基金
中国国家自然科学基金;
关键词
Biocatalysis; Lactams; Carboxylic acid reductase; Intramolecular cyclization; Lactamization; ALDEHYDE OXIDOREDUCTASE; GAMMA-LACTAMS; STRAIN; ENZYME;
D O I
10.1016/j.gresc.2022.05.009
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
As a versatile type of enzyme, carboxylic acid reductases (CAR) can not only reduce various carboxylic acids to aldehydes in cooperation with cofactors ATP and NADPH but also catalyze the synthesis of amides and esters in the absence of NADPH. Here, we report an intramolecular cyclization catalyzed by CAR only with the use of ATP to transform amino acids into diverse lactams, including & gamma;-/& delta;-/& epsilon;-lactams and chiral derivatives thereof. The observed wide substrate scope and selectivity enable potential applications to be implemented. Our results demonstrate that CAR-catalyzed lactamization is a promising approach for the synthesis of chiral lactam compounds under mild conditions, thereby enriching the toolbox for the biosynthesis of lactams as a viable alternative to purely chemical procedures.
引用
收藏
页码:294 / 297
页数:4
相关论文
共 50 条
[41]   Identification, Characterization, and Application of Three Enoate Reductases from Pseudomonas putida in In Vitro Enzyme Cascade Reactions [J].
Peters, Christin ;
Koelzsch, Regina ;
Kadow, Maria ;
Skalden, Lilly ;
Rudroff, Florian ;
Mihovilovic, Marko D. ;
Bornscheuer, Uwe T. .
CHEMCATCHEM, 2014, 6 (04) :1021-1027
[42]   Engineering carboxylic acid reductase for selective synthesis of medium-chain fatty alcohols in yeast [J].
Hu, Yating ;
Zhu, Zhiwei ;
Gradischnig, David ;
Winkler, Margit ;
Nielsen, Jens ;
Siewers, Verena .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2020, 117 (37) :22974-22983
[43]   N-substituted pyrrole carboxylic acid derivatives from 3,4-dihydroxyketons [J].
Laudage, Tatjana ;
Huesing, Torben ;
Ruehmann, Broder ;
Beer, Barbara ;
Schmermund, Luca ;
Sieber, Volker .
CHEMSUSCHEM, 2024, 17 (09)
[44]   Biocatalyst Immobilization and Process Intensification: Production of (S)-Piperazine-2-carboxylic Acid Dihydrochloride [J].
Padrosa, David Roura ;
Wetzl, Dennis ;
Hildbrand, Stefan ;
Tosatti, Paolo ;
Sedelmeier, Joerg ;
Puentener, Kurt ;
Iding, Hans ;
Paradisi, Francesca .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2024, 28 (05) :1713-1724
[45]   Cofactor-Driven Cascade Reactions Enable the Efficient Preparation of Sugar Nucleotides [J].
Zheng, Yuan ;
Zhang, Jiabin ;
Meisner, Jeffrey ;
Li, Wanjin ;
Luo, Yawen ;
Wei, Fangyu ;
Wen, Liuqing .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (20)
[46]   Dual Activation Modes Enable Bifunctional Catalysis of Aldol Reactions by Flexible Dihydrazides [J].
Lampkin, Philip P. ;
Gellman, Samuel H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2025, 147 (04) :3731-3739
[47]   Heterogeneous Au and Rh catalysts for cycloisomerization reactions of γ-acetylenic carboxylic acids [J].
Neatu, Florentina ;
Toullec, Patrick Y. ;
Michelet, Veronique ;
Parvulescu, Vasile I. .
PURE AND APPLIED CHEMISTRY, 2009, 81 (12) :2387-2396
[48]   Multicomponent synthesis of pyroglutamic acid derivatives via Knoevenagel-Michael-hydrolysis-lactamization-decarboxylation (KMHL-D) sequence [J].
Khopade, Tushar M. ;
Warghude, Prakash K. ;
Sonawane, Amol D. ;
Bhat, Ramakrishna G. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (03) :561-566
[49]   One-Pot Cascade Synthesis of Mono- and Disubstituted Piperidines and Pyrrolidines using Carboxylic Acid Reductase (CAR), ω-Transaminase (ω-TA), and Imine Reductase (IRED) Biocatalysts [J].
France, Scott P. ;
Hussain, Shahed ;
Hill, Andrew M. ;
Hepworth, Lorna J. ;
Howard, Roger M. ;
Mulholland, Keith R. ;
Flitsch, Sabine L. ;
Turner, Nicholas J. .
ACS CATALYSIS, 2016, 6 (06) :3753-3759
[50]   Enzymatic Synthesis of Aliphatic Primary ω-Amino Alcohols from ω-Amino Fatty Acids by Carboxylic Acid Reductase [J].
Sarak, Sharad ;
Jeon, Hyunwoo ;
Patil, Mahesh D. ;
Khobragade, Taresh P. ;
Pagar, Amol D. ;
Sung, Sihyong ;
Yoo, Hee-Wang ;
Kim, Byung-Gee ;
Yoon, Sung Ho ;
Yun, Hyungdon .
CATALYSIS LETTERS, 2020, 150 (11) :3079-3085