Issue 4, 2016

Laccase-catalysed biotransformation of collismycin derivatives. A novel enzymatic approach for the cleavage of oximes

Abstract

Analogues of the natural product collismycin bearing a carboxylic acid moiety has been efficiently synthesised from several collismycin precursors through a laccase-catalysed oxidation under mild conditions with TEMPO (2,2,6,6-tetramethylpiperidin-1-oxyl) as a mediator and aerial O2 as an oxidant in aqueous medium. The biotransformations proceeded with excellent yields (85–95%) and involved, depending on the precursor, the oxidation of a benzylic hydroxyl group or the bioconversion of an aldoxime group into carboxylic acid. Since the latter is herein reported for the first time, we explored the potential of this novel oxime cleavage with several synthetic aldo- and ketoximes. Thus, the laccase/TEMPO system proved to be an efficient and green alternative for the deprotection of both aromatic and aliphatic ketoximes into the corresponding ketones. On the other hand, the reaction with aldoximes leads to dimeric species generated by coupling reactions.

Graphical abstract: Laccase-catalysed biotransformation of collismycin derivatives. A novel enzymatic approach for the cleavage of oximes

Supplementary files

Article information

Article type
Communication
Submitted
16 Sep 2015
Accepted
16 Oct 2015
First published
16 Oct 2015

Green Chem., 2016,18, 989-994

Laccase-catalysed biotransformation of collismycin derivatives. A novel enzymatic approach for the cleavage of oximes

J. González-Sabín, N. Ríos-Lombardía, I. García, N. M. Vior, A. F. Braña, C. Méndez, J. A. Salas and F. Morís, Green Chem., 2016, 18, 989 DOI: 10.1039/C5GC02220G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements