Rational design of mimetic peptides based on aldo-ketoreductase enzyme as asymmetric organocatalysts in aldol reactions

被引：11

作者：

Bayat, Saadi ^{[1
,2
]}

Tejo, Bimo A. ^{[3
]}

Abdulmalek, Emilia ^{[1
,2
]}

Salleh, Abu Bakar ^{[1
]}

Normi, Yahaya M. ^{[1
]}

Rahman, Mohd Basyaruddin Abdul ^{[1
,2
]}

机构：

[1] Univ Putra Malaysia, Enzyme & Microbial Technol Res Ctr, Serdang 43400, Malaysia

[2] Univ Putra Malaysia, Fac Sci, Dept Chem, Serdang 43400, Malaysia

[3] Surya Univ, Ctr Infect Dis Res, Banten 15810, Indonesia

来源：

RSC ADVANCES | 2014年 / 4卷 / 73期

关键词：

PROTEIN SECONDARY STRUCTURE; KETO REDUCTASE SUPERFAMILY; PROLINE-BASED DIPEPTIDES; MICHAEL ADDITION; CATALYSTS; WATER; SPECTROSCOPY; TRIPEPTIDES; ALDEHYDES; EFFICIENT;

D O I：

10.1039/c4ra04866k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Peptides as a kind of important chiral scaffold are broadly identified for their obvious advantages, diverse structures and accessibility. Based on promiscuous aldo-keto-reductase enzymes, several mimetic peptides were designed which were synthesized and tested as multifunctional organocatalysts in direct asymmetric aldol reactions. The corresponding aldol products were produced with high yields (up to 97%) and excellent diastereoselectivities (up to 99/1) and enantioselectivities (>98%) under mild reaction selectivity and enantioselectivity. The secondary structures of peptide catalysts provide an understanding of their mechanism.

引用

页码：38859 / 38868

页数：10

共 21 条

[1] Asymmetric aldol reactions catalyzed by the promiscuous aldo-ketoreductase enzyme
Bayat, Saadi
Abd Malek, Emilia
Yahaya, Normi M.
Salleh, Abu Bakar
Tejo, Bimo Ario
Rahman, Mohd Basyaruddin Abdul
TETRAHEDRON LETTERS, 2014, 55 (46) : 6303 - 6306
[2] Design of organocatalysts for asymmetric direct syn-aldol reactions
Xu, Xiao-Ying
Wang, Yan-Zhao
Gong, Liu-Zhu
ORGANIC LETTERS, 2007, 9 (21) : 4247 - 4249
[3] Design of a Simple Organocatalysts for Asymmetric Direct Aldol Reactions in Aqueous Medium
Bayat, Saadi
Salleh, Abu Bakar
Malek, Emilia Abd
Yousefi, Samira
Rahman, Mohd Basyaruddin Abdul
CATALYSIS LETTERS, 2015, 145 (09) : 1750 - 1755
[4] Design of a Simple Organocatalysts for Asymmetric Direct Aldol Reactions in Aqueous Medium
Saadi Bayat
Abu Bakar Salleh
Emilia Abd Malek
Samira Yousefi
Mohd Basyaruddin Abdul Rahman
Catalysis Letters, 2015, 145 : 1750 - 1755
[5] Chiral Thiazolidine based Organocatalysts: Synthesis and Application in Asymmetric Aldol Reactions
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Simoes, Pedro R. D.
Sousa, Francisco J. P. M.
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LETTERS IN ORGANIC CHEMISTRY, 2020, 17 (05) : 372 - 380
[6] Polymer Supported Proline-Based Organocatalysts in Asymmetric Aldol Reactions: A Review
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Sarang, Rithwik
Saithalavi, Anas
CURRENT ORGANOCATALYSIS, 2022, 9 (02) : 124 - 146
[7] Proline-based dipeptides as efficient organocatalysts for asymmetric aldol reactions in brine
Tian, Hua
Gao, Jun-long
Xu, Hao
Zheng, Liang-Yu
Huang, Wen-Bo
Liu, Qing-Wen
Zhang, Suo-Qin
TETRAHEDRON-ASYMMETRY, 2011, 22 (10) : 1074 - 1080
[8] Design and synthesis of novel chiral organocatalysts and their application in solvent-free asymmetric aldol and Michael reactions
Vega-Penaloza, Alberto
Avila-Ortiz, Claudia G.
Sanchez-Antonio, Omar
Juaristi, Eusebio
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
[9] Novel Axially Unfixed Biaryl-Based Water-Compatible Organocatalysts: Design, Synthesis and Their Asymmetric Catalysis in Direct Aldol Reactions in Water
Zhao, Hong-Wu
Yue, Yuan-Yuan
Li, Hai-Long
Song, Xiu-Qing
Sheng, Zhi-Hui
Yang, Zhao
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Yang, Ze
SYNLETT, 2013, 24 (16) : 2160 - 2164
[10] Rational combination of two privileged chiral backbones: Highly efficient organocatalysts for asymmetric direct aldol reactions between aromatic aldehydes and acylic ketones
Chen, Jia-Rong
An, Xiao-Lei
Zhu, Xiao-Yu
Wang, Xu-Fan
Xiao, Wen-Jing
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (15): : 6006 - 6009

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