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Stereochemistry of Delta4 dehydrogenation catalyzed by an ivy (Hedera helix) Delta9 desaturase homolog.

Authors :
Tremblay AE
Whittle E
Buist PH
Shanklin J
Source :
Organic & biomolecular chemistry [Org Biomol Chem] 2007 Apr 21; Vol. 5 (8), pp. 1270-5. Date of Electronic Publication: 2007 Mar 19.
Publication Year :
2007

Abstract

The stereochemistry of palmitoyl-ACP Delta(4) desaturase-mediated dehydrogenation has been examined by tracking the fate of deuterium atoms located on stereospecifically monodeuterated substrates-(4S)- and (4R)-[4-(2)H(1)]-palmitoyl-ACP and (5S)- and (5R)-[5-(2)H(1)]-palmitoyl-ACP. It was found that the introduction of the (Z)-double bond between C-4 and C-5 of a palmitoyl substrate occurs with pro-R enantioselectivity-a result which matches that obtained for a closely related homolog-castor stearoyl-ACP Delta(9) desaturase. These data show that despite the difference in regioselectivity between the two enzymes, the stereochemistry of hydrogen removal is conserved.

Details

Language :
English
ISSN :
1477-0520
Volume :
5
Issue :
8
Database :
MEDLINE
Journal :
Organic & biomolecular chemistry
Publication Type :
Academic Journal
Accession number :
17406726
Full Text :
https://doi.org/10.1039/b617942h