Toggle Main Menu Toggle Search

Open Access padlockePrints

A Natural Diels-Alder Biocatalyst Enables Efficient [4+2] Cycloaddition Under Harsh Reaction Conditions

Lookup NU author(s): Dr James StachORCiD, Professor Paul RaceORCiD

Downloads


Licence

This is the authors' accepted manuscript of an article that has been published in its final definitive form by Wiley Blackwell, 2019.

For re-use rights please refer to the publisher's terms and conditions.


Abstract

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, WeinheimCarbon-carbon bond formation is a fundamental transformation in both synthetic chemistry and biosynthesis. Enzymes catalyze such reactions with exquisite selectivity which often cannot be achieved using non-biological methods but may suffer from an intolerance of high temperature and the presence of organic solvents limiting their applications. Here we report the thermodynamic and kinetic stability of the β-barrel natural Diels-Alderase AbyU, which catalyzes formation of the spirotetronate core of the antimicrobial natural product abyssomicin C, with creation of 3 new asymmetric centers. This enzyme is shown to catalyze [4+2] cycloadditions at elevated temperature (up to 65 °C), and in the presence of organic solvents (MeOH, CH3CN and DMSO) and the chemical denaturant guanidinium hydrochloride, revealing that AbyU has potential widespread value as a biocatalyst.


Publication metadata

Author(s): Marsh CO, Lees NR, Han L-C, Byrne MJ, Mbatha SZ, Maschio L, Pagden-Ratcliffe S, Duke PW, Stach JEM, Curnow P, Willis CL, Race PR

Publication type: Article

Publication status: Published

Journal: ChemCatChem

Year: 2019

Volume: 11

Issue: 20

Pages: 5027-5031

Print publication date: 01/10/2019

Online publication date: 25/08/2019

Acceptance date: 21/08/2019

Date deposited: 07/11/2019

ISSN (print): 1867-3880

ISSN (electronic): 1867-3899

Publisher: Wiley Blackwell

URL: https://doi.org/10.1002/cctc.201901285

DOI: 10.1002/cctc.201901285


Altmetrics

Altmetrics provided by Altmetric


Funding

Funder referenceFunder name
BB/L01386X/1
BB/I006478/1
BB/M025624/1
EP/G0367641/1
DSTLX1000098188
EP/L016494/1

Share