Synthesis of highly enantioenriched hydroxy- and dihydroxy-fatty esters: substrate precursors for cytochrome P450(BioI)

Singh, Arti A., Zulkifli, Siti N. A., Meyns, Michaela, Hayes, Patricia Y. and De Voss, James J. (2011) Synthesis of highly enantioenriched hydroxy- and dihydroxy-fatty esters: substrate precursors for cytochrome P450(BioI). Tetrahedron-Asymmetry, 22 18-19: 1709-1719. doi:10.1016/j.tetasy.2011.08.027


Author Singh, Arti A.
Zulkifli, Siti N. A.
Meyns, Michaela
Hayes, Patricia Y.
De Voss, James J.
Title Synthesis of highly enantioenriched hydroxy- and dihydroxy-fatty esters: substrate precursors for cytochrome P450(BioI)
Formatted title
Synthesis of highly enantioenriched hydroxy- and dihydroxy-fatty esters: Substrate precursors for cytochrome P450BioI
Journal name Tetrahedron-Asymmetry   Check publisher's open access policy
ISSN 0957-4166
1362-511X
Publication date 2011-10-15
Year available 2011
Sub-type Article (original research)
DOI 10.1016/j.tetasy.2011.08.027
Volume 22
Issue 18-19
Start page 1709
End page 1719
Total pages 11
Place of publication East Park, Kidlington, Oxford, U.K.
Publisher Pergamon
Collection year 2012
Language eng
Formatted abstract
A series of highly enantioenriched hydroxy- and dihydroxy-fatty esters were required as part of our ongoing investigation into cytochrome P450BioI. This mediates the biosynthesis of pimelic acid via C–C bond cleavage of long chain fatty acids within Bacillus subtilis. Herein we report the synthesis of various stereoisomers of methyl 7-hydroxytetradecanoate, methyl 8-hydroxytetradecanoate, and methyl 7,8-dihydroxytetradecanoate in highly enantioenriched form, using a combination of asymmetric synthesis and a preparative enantioselective HPLC is reported.
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2012 Collection
School of Chemistry and Molecular Biosciences
 
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Created: Tue, 07 Feb 2012, 08:20:48 EST by Lucy O'Brien on behalf of School of Chemistry & Molecular Biosciences