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author:

Guo, Zijun (Guo, Zijun.) [1] | Wu, Zexin (Wu, Zexin.) [2] | Wu, Xiaofan (Wu, Xiaofan.) [3] | Zhang, Li (Zhang, Li.) [4] | Huang, Zedu (Huang, Zedu.) [5] | Chen, Fener (Chen, Fener.) [6]

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EI Scopus SCIE

Abstract:

Owing to its associated advantages such as the generation of two stereocenters in 100% maximum theoretical yield, mild reaction conditions and environmentally friendliness, ketoreductase (KRED)-catalyzed dynamic reductive kinetic resolution (DYRKR) is a versatile and appealing synthetic approach to access valuable chiral alcohols containing two or more stereocenters. Despite the considerable progress that has been made in this research field, previous studies mostly focused on ketone substrates with relatively simple structures. In the present study, ketoreductases YDR368w and YGL039w were identified through enzyme screening and applied to the KRED-catalyzed DYRKR of sterically hindered 2-aryl-1,5-benzothiazepin-3,4(2H,5H)-diones (1). Eleven structurally diverse chiral cis-(2S,3S)-2,3-dihydro-3-hydroxy-2-aryl-1,5-benzothiazepin-4(5H)-ones (cis-(2S,3S)-2), including the critical synthetic intermediates to the calcium channel blockers diltiazem and clentiazem, were prepared in 50-90% isolated yields with excellent stereoselectivities (all >20 : 1 dr and >= 99% ee). Finally, the successful execution of a gram scale synthesis and the demonstrated excellent recyclability of the immobilized ketoreductase (up to 20 cycles) both underscored the good application potential of the currently established DYRKR method.

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Community:

  • [ 1 ] [Guo, Zijun]Fuzhou Univ, Coll Biol Sci & Engn, Fuzhou 350116, Peoples R China
  • [ 2 ] [Wu, Zexin]Fuzhou Univ, Coll Biol Sci & Engn, Fuzhou 350116, Peoples R China
  • [ 3 ] [Chen, Fener]Fuzhou Univ, Coll Biol Sci & Engn, Fuzhou 350116, Peoples R China
  • [ 4 ] [Wu, Xiaofan]Fudan Univ, Engn Ctr Catalysis & Synth Chiral Mol, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China
  • [ 5 ] [Huang, Zedu]Fudan Univ, Engn Ctr Catalysis & Synth Chiral Mol, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China
  • [ 6 ] [Chen, Fener]Fudan Univ, Engn Ctr Catalysis & Synth Chiral Mol, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China
  • [ 7 ] [Wu, Xiaofan]Shanghai Engn Res Ctr Ind Asymmetr Catalysis Chira, 220 Handan Rd, Shanghai 200433, Peoples R China
  • [ 8 ] [Huang, Zedu]Shanghai Engn Res Ctr Ind Asymmetr Catalysis Chira, 220 Handan Rd, Shanghai 200433, Peoples R China
  • [ 9 ] [Chen, Fener]Shanghai Engn Res Ctr Ind Asymmetr Catalysis Chira, 220 Handan Rd, Shanghai 200433, Peoples R China
  • [ 10 ] [Zhang, Li]Zhengzhou Univ, Sch Pharmaceut Sci, Zhengzhou 450001, Peoples R China
  • [ 11 ] [Chen, Fener]Zhengzhou Univ, Sch Pharmaceut Sci, Zhengzhou 450001, Peoples R China
  • [ 12 ] [Chen, Fener]Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Peoples R China

Reprint 's Address:

  • [Chen, Fener]Fuzhou Univ, Coll Biol Sci & Engn, Fuzhou 350116, Peoples R China;;[Huang, Zedu]Fudan Univ, Engn Ctr Catalysis & Synth Chiral Mol, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China;;[Chen, Fener]Fudan Univ, Engn Ctr Catalysis & Synth Chiral Mol, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China;;[Huang, Zedu]Shanghai Engn Res Ctr Ind Asymmetr Catalysis Chira, 220 Handan Rd, Shanghai 200433, Peoples R China;;[Chen, Fener]Shanghai Engn Res Ctr Ind Asymmetr Catalysis Chira, 220 Handan Rd, Shanghai 200433, Peoples R China;;[Chen, Fener]Zhengzhou Univ, Sch Pharmaceut Sci, Zhengzhou 450001, Peoples R China;;[Chen, Fener]Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Peoples R China;;

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Source :

GREEN CHEMISTRY

ISSN: 1463-9262

Year: 2024

Issue: 13

Volume: 26

Page: 7818-7824

9 . 3 0 0

JCR@2023

Cited Count:

WoS CC Cited Count:

SCOPUS Cited Count:

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 1

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