Efficient Enzymatic Synthesis of Carbamates in Water Using Promiscuous Esterases/Acyltransferases

Angew Chem Int Ed Engl. 2024 Jul 22;63(30):e202405152. doi: 10.1002/anie.202405152. Epub 2024 Jun 21.

Abstract

Biocatalysis provides an attractive approach to facilitate synthetic reactions in aqueous media. Motivated by the discovery of promiscuous aminolysis activity of esterases, we exploited the esterase from Pyrobaculum calidifontis VA1 (PestE) for the synthesis of carbamates from different aliphatic, aromatic, and arylaliphatic amines and a set of carbonates such as dimethyl-, dibenzyl-, or diallyl carbonate. Thus, aniline and benzylamine derivatives, aliphatic and even secondary amines could be efficiently converted into the corresponding benzyloxycarbonyl (Cbz)- or allyloxycarbonyl (Alloc)-protected products in bulk water, with (isolated) yields of up to 99 %.

Keywords: Acyltransferase; Amine; Biocatalysis; Carbamate; Esterase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acyltransferases* / chemistry
  • Acyltransferases* / metabolism
  • Amines / chemistry
  • Amines / metabolism
  • Biocatalysis
  • Carbamates* / chemical synthesis
  • Carbamates* / chemistry
  • Carbamates* / metabolism
  • Esterases* / chemistry
  • Esterases* / metabolism
  • Molecular Structure
  • Water* / chemistry

Substances

  • Esterases
  • Carbamates
  • Water
  • Acyltransferases
  • Amines

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