Advanced

Exploring the Substrate Specificity and Enantioselectivity of a Baeyer-Villiger Monooxygenase from Dietzia sp D5: Oxidation of Sulfides and Aldehydes

Bisagni, Serena LU ; Summers, Benjamin; Kara, Selin; Hatti-Kaul, Rajni LU ; Grogan, Gideon; Mamo, Gashaw LU and Hollmann, Frank (2014) In Topics in Catalysis 57(5). p.366-375
Abstract
Baeyer-Villiger monooxygenases (BVMOs) are valuable enzymes for specific oxyfunctionalization chemistry. They catalyze the oxidation of ketones to esters, but are also capable of oxidizing other chemical functions, namely aldehydes and heteroatoms such as sulfur, nitrogen, selenium and boron. The oxidation specificity and enantioselectivity of a newly characterized BVMO (BVMO4) from a strain of Dietzia towards sulfide- and aldehyde substrates have been studied. BVMO4 could react with sulfides containing an aromatic group. The presence of a substituent on the aromatic group was tolerated when they were in the meta- and para position and the oxidations yielded predominantly the (R)-sulfoxides. Similarly, BVMO4 displayed a higher activity for... (More)
Baeyer-Villiger monooxygenases (BVMOs) are valuable enzymes for specific oxyfunctionalization chemistry. They catalyze the oxidation of ketones to esters, but are also capable of oxidizing other chemical functions, namely aldehydes and heteroatoms such as sulfur, nitrogen, selenium and boron. The oxidation specificity and enantioselectivity of a newly characterized BVMO (BVMO4) from a strain of Dietzia towards sulfide- and aldehyde substrates have been studied. BVMO4 could react with sulfides containing an aromatic group. The presence of a substituent on the aromatic group was tolerated when they were in the meta- and para position and the oxidations yielded predominantly the (R)-sulfoxides. Similarly, BVMO4 displayed a higher activity for aldehydes containing a phenyl group, but long aliphatic aldehydes, namely octanal and decanal, were also accepted as substrate by this enzyme. The major oxidation products of the aldehyde substrates were the respective carboxylic acids in contrast to formate ester that was obtained in most of the previous reports. The Baeyer-Villiger oxidation of the substrate 2-phenylpropionaldehyde was studied in further detail and the corresponding acid product was obtained with good regio- and enantioselectivity. This is a unique feature for BVMO4 and is of great interest for further exploration of an alternative biocatalytic process. (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
Baeyer-Villiger monooxygenase, 2-Phenylpropionaldehyde, Dietzia, Profen, Biocatalysis
in
Topics in Catalysis
volume
57
issue
5
pages
366 - 375
publisher
Kluwer
external identifiers
  • wos:000331698100009
  • scopus:84896561683
ISSN
1572-9028
DOI
10.1007/s11244-013-0192-1
language
English
LU publication?
yes
id
c703d339-cb0f-4a8b-8528-bc2de9523dfb (old id 4417795)
date added to LUP
2014-05-05 11:19:27
date last changed
2017-08-27 04:31:58
@article{c703d339-cb0f-4a8b-8528-bc2de9523dfb,
  abstract     = {Baeyer-Villiger monooxygenases (BVMOs) are valuable enzymes for specific oxyfunctionalization chemistry. They catalyze the oxidation of ketones to esters, but are also capable of oxidizing other chemical functions, namely aldehydes and heteroatoms such as sulfur, nitrogen, selenium and boron. The oxidation specificity and enantioselectivity of a newly characterized BVMO (BVMO4) from a strain of Dietzia towards sulfide- and aldehyde substrates have been studied. BVMO4 could react with sulfides containing an aromatic group. The presence of a substituent on the aromatic group was tolerated when they were in the meta- and para position and the oxidations yielded predominantly the (R)-sulfoxides. Similarly, BVMO4 displayed a higher activity for aldehydes containing a phenyl group, but long aliphatic aldehydes, namely octanal and decanal, were also accepted as substrate by this enzyme. The major oxidation products of the aldehyde substrates were the respective carboxylic acids in contrast to formate ester that was obtained in most of the previous reports. The Baeyer-Villiger oxidation of the substrate 2-phenylpropionaldehyde was studied in further detail and the corresponding acid product was obtained with good regio- and enantioselectivity. This is a unique feature for BVMO4 and is of great interest for further exploration of an alternative biocatalytic process.},
  author       = {Bisagni, Serena and Summers, Benjamin and Kara, Selin and Hatti-Kaul, Rajni and Grogan, Gideon and Mamo, Gashaw and Hollmann, Frank},
  issn         = {1572-9028},
  keyword      = {Baeyer-Villiger monooxygenase,2-Phenylpropionaldehyde,Dietzia,Profen,Biocatalysis},
  language     = {eng},
  number       = {5},
  pages        = {366--375},
  publisher    = {Kluwer},
  series       = {Topics in Catalysis},
  title        = {Exploring the Substrate Specificity and Enantioselectivity of a Baeyer-Villiger Monooxygenase from Dietzia sp D5: Oxidation of Sulfides and Aldehydes},
  url          = {http://dx.doi.org/10.1007/s11244-013-0192-1},
  volume       = {57},
  year         = {2014},
}