Jump to main content
Jump to site search


Mono-substitution of symmetric diesters: selectivity of Mycobacterium smegmatis acyltransferase variants

Author affiliations

Abstract

A method for selectively reacting one, out of two identical carboxylic esters in a symmetric diester has been developed. An esterase from Mycobacterium smegmatis (MsAcT) has a restricted active site resulting in a narrow acyl donor specificity. This constraint was used to develop a selective synthesis route from divinyl adipate (a symmetric diester) towards mixed vinyl adipate esters. To find a suitable catalyst, the wild type (wt) MsAcT and two MsAcT variants: a single point mutant (L12A) and a double point mutant (T93A/F154A), were immobilized and studied under solvent-free conditions. Out of the tested catalysts, MsAcT L12A was the most selective for mono-transesterification of divinyl adipate. When divinyl adipate was reacted with 1.5 equivalents of a hydroxyl vinyl ether full conversion of DVA was observed yielding over 95% mixed diester. Furthermore, the limitations for longer dicarboxylic esters were studied, showing that MsAcT T93A/F154A tolerated up to at least dimethyl sebacate.

Graphical abstract: Mono-substitution of symmetric diesters: selectivity of Mycobacterium smegmatis acyltransferase variants

Back to tab navigation

Supplementary files

Publication details

The article was received on 16 Jun 2019, accepted on 09 Aug 2019 and first published on 09 Aug 2019


Article type: Paper
DOI: 10.1039/C9CY01181A
Catal. Sci. Technol., 2019, Advance Article
  • Open access: Creative Commons BY license
  •   Request permissions

    Mono-substitution of symmetric diesters: selectivity of Mycobacterium smegmatis acyltransferase variants

    M. Finnveden, S. Semlitsch, O. He and M. Martinelle, Catal. Sci. Technol., 2019, Advance Article , DOI: 10.1039/C9CY01181A

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements