Details
| Original language | English |
|---|---|
| Pages (from-to) | 366-375 |
| Number of pages | 10 |
| Journal | Topics in catalysis |
| Volume | 57 |
| Issue number | 5 |
| Early online date | 16 Nov 2013 |
| Publication status | Published - Mar 2014 |
| Externally published | Yes |
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.
Keywords
- 2-Phenylpropionaldehyde, Baeyer-Villiger monooxygenase, Biocatalysis, Dietzia, Profen
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- General Chemistry
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In: Topics in catalysis, Vol. 57, No. 5, 03.2014, p. 366-375.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Exploring the substrate specificity and enantioselectivity of a baeyer-villiger monooxygenase from dietzia sp. D5
T2 - Oxidation of sulfides and aldehydes
AU - Bisagni, Serena
AU - Summers, Benjamin
AU - Kara, Selin
AU - Hatti-Kaul, Rajni
AU - Grogan, Gideon
AU - Mamo, Gashaw
AU - Hollmann, Frank
PY - 2014/3
Y1 - 2014/3
N2 - 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.
AB - 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.
KW - 2-Phenylpropionaldehyde
KW - Baeyer-Villiger monooxygenase
KW - Biocatalysis
KW - Dietzia
KW - Profen
UR - http://www.scopus.com/inward/record.url?scp=84896561683&partnerID=8YFLogxK
U2 - 10.1007/s11244-013-0192-1
DO - 10.1007/s11244-013-0192-1
M3 - Article
AN - SCOPUS:84896561683
VL - 57
SP - 366
EP - 375
JO - Topics in catalysis
JF - Topics in catalysis
SN - 1022-5528
IS - 5
ER -