Please use this identifier to cite or link to this item: https://doi.org/10.1021/acscatal.8b02713
Title: Amide Synthesis via Aminolysis of Ester or Acid with an Intracellular Lipase
Authors: Zeng, Shichao
Liu, Ji 
Anankanbil, Sampson
Chen, Ming 
Guo, Zheng
Adams, Joseph P
Snajdrova, Radka
Li, Zhi 
Keywords: Science & Technology
Physical Sciences
Chemistry, Physical
Chemistry
amide synthesis
aminolysis of ester
aminolysis of acid
enzyme catalysis
intracellular lipase
whole cells
ACINETOBACTER-CALCOACETICUS BD413
ACYLASE-CATALYZED RESOLUTION
SPHINGOMONAS SP HXN-200
ORGANIC-SOLVENTS
WASTE GREASE
ENZYMATIC-SYNTHESIS
ONE-POT
ENANTIOSELECTIVE HYDROLYSIS
NITROGEN NUCLEOPHILES
EXTRACELLULAR LIPASE
Issue Date: 1-Sep-2018
Publisher: AMER CHEMICAL SOC
Citation: Zeng, Shichao, Liu, Ji, Anankanbil, Sampson, Chen, Ming, Guo, Zheng, Adams, Joseph P, Snajdrova, Radka, Li, Zhi (2018-09-01). Amide Synthesis via Aminolysis of Ester or Acid with an Intracellular Lipase. ACS CATALYSIS 8 (9) : 8856-8865. ScholarBank@NUS Repository. https://doi.org/10.1021/acscatal.8b02713
Abstract: © 2018 American Chemical Society. A unique lipase (SpL) from Sphingomonas sp. HXN-200 was discovered as the first intracellular enzyme for the aminolysis of ester or acid to produce amide. Reactions of a series of esters and amines with SpL gave the corresponding amides 3a-g in high yield with high activity. SpL also showed high enantioselectivity and high activity for enantioselective ester aminolysis, producing amides (R)-3h-j in high ee from the corresponding racemic ester or amine. Moreover, SpL was found to be highly active for the aminolysis of carboxylic acid, which was generally considered infeasible with the known aminolysis enzymes. The aminolysis of several carboxylic acids afforded the corresponding amides 3a, 3d, 3k, 3l, and 3n in good yield. The intracellular SpL was expressed in Escherichia coli cells to give an efficient whole-cell biocatalyst for amide synthesis. Remarkably, high catalytic activity was observed in the presence of water at 2-4% (v/v) for free enzyme and 16% (v/v) for whole cells, respectively. Accordingly, E. coli (SpL) wet cells were used as easily available and practical catalysts for the aminolysis of ester or acid, producing a group of useful and valuable amides in high concentration (up to 103 mM) and high yield. The newly discovered intracellular SpL with unique properties is a promising catalyst for green and efficient synthesis of amides.
Source Title: ACS CATALYSIS
URI: https://scholarbank.nus.edu.sg/handle/10635/155372
ISSN: 2155-5435
2155-5435
DOI: 10.1021/acscatal.8b02713
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