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A Bi-enzymatic Convergent Cascade for epsilon-Caprolactone Synthesis Employing 1,6-Hexanediol as a "Double-Smart Cosubstrate'

Bornadel, Amin; Hatti-Kaul, Rajni LU ; Hollmann, Frank and Kara, Selin (2015) In ChemCatChem 7(16). p.2442-2445
Abstract
A bi-enzymatic cascade consisting of a Baeyer-Villiger monooxygenase and an alcohol dehydrogenase (ADH) was designed in a convergent fashion to utilise two molar equivalents of cyclohexanone (CHO) and one equivalent of 1,6-hexanediol as a 'double-smart cosubstrate' to produce epsilon-caprolactone (ECL) with water as sole by-product. The convergent enzymatic cascade reaction reported herein, is performed at ambient conditions in water, is self-sufficient with respect to cofactor, and incorporates all starting materials into the desired product, ECL. Among different enzymes explored, the reaction catalysed by cyclohexanone monooxygenase from Acinetobacter sp. NCIMB 9871 coupled with ADH from Thermoanaerobacter ethanolicus showed the best... (More)
A bi-enzymatic cascade consisting of a Baeyer-Villiger monooxygenase and an alcohol dehydrogenase (ADH) was designed in a convergent fashion to utilise two molar equivalents of cyclohexanone (CHO) and one equivalent of 1,6-hexanediol as a 'double-smart cosubstrate' to produce epsilon-caprolactone (ECL) with water as sole by-product. The convergent enzymatic cascade reaction reported herein, is performed at ambient conditions in water, is self-sufficient with respect to cofactor, and incorporates all starting materials into the desired product, ECL. Among different enzymes explored, the reaction catalysed by cyclohexanone monooxygenase from Acinetobacter sp. NCIMB 9871 coupled with ADH from Thermoanaerobacter ethanolicus showed the best results, reaching 91% conversion of CHO after 24h with a product titre of 2gL(-1). Scale-up of the coupled system (50mL) performed better than the small-scale reactions and >99% conversion of CHO and ECL concentration of 20mM were achieved within 18h. (Less)
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
alcohol dehydrogenases, caprolactone, Baeyer-Villiger reaction, monooxygenases, multi-enzymatic cascades, smart cosubstrate
in
ChemCatChem
volume
7
issue
16
pages
2442 - 2445
publisher
John Wiley & Sons
external identifiers
  • wos:000359765200006
  • scopus:84939149187
ISSN
1867-3880
DOI
10.1002/cctc.201500511
language
English
LU publication?
yes
id
cd2902c8-ba5d-4bad-b425-e2d2d3eea54d (old id 7975517)
date added to LUP
2015-09-24 14:37:04
date last changed
2017-09-24 03:14:20
@article{cd2902c8-ba5d-4bad-b425-e2d2d3eea54d,
  abstract     = {A bi-enzymatic cascade consisting of a Baeyer-Villiger monooxygenase and an alcohol dehydrogenase (ADH) was designed in a convergent fashion to utilise two molar equivalents of cyclohexanone (CHO) and one equivalent of 1,6-hexanediol as a 'double-smart cosubstrate' to produce epsilon-caprolactone (ECL) with water as sole by-product. The convergent enzymatic cascade reaction reported herein, is performed at ambient conditions in water, is self-sufficient with respect to cofactor, and incorporates all starting materials into the desired product, ECL. Among different enzymes explored, the reaction catalysed by cyclohexanone monooxygenase from Acinetobacter sp. NCIMB 9871 coupled with ADH from Thermoanaerobacter ethanolicus showed the best results, reaching 91% conversion of CHO after 24h with a product titre of 2gL(-1). Scale-up of the coupled system (50mL) performed better than the small-scale reactions and >99% conversion of CHO and ECL concentration of 20mM were achieved within 18h.},
  author       = {Bornadel, Amin and Hatti-Kaul, Rajni and Hollmann, Frank and Kara, Selin},
  issn         = {1867-3880},
  keyword      = {alcohol dehydrogenases,caprolactone,Baeyer-Villiger reaction,monooxygenases,multi-enzymatic cascades,smart cosubstrate},
  language     = {eng},
  number       = {16},
  pages        = {2442--2445},
  publisher    = {John Wiley & Sons},
  series       = {ChemCatChem},
  title        = {A Bi-enzymatic Convergent Cascade for epsilon-Caprolactone Synthesis Employing 1,6-Hexanediol as a "Double-Smart Cosubstrate'},
  url          = {http://dx.doi.org/10.1002/cctc.201500511},
  volume       = {7},
  year         = {2015},
}