In:
ChemBioChem, Wiley, Vol. 17, No. 15 ( 2016-08-03), p. 1426-1429
Abstract:
The bacterial pathway of olefin biosynthesis starts with OleA catalyzed “head‐to‐head” condensation of two CoA‐activated long‐chain fatty acids to generate ( R )‐2‐alkyl‐3‐ketoalkanoic acids. A subsequent OleD‐catalyzed reduction generates (2 R ,3 S )‐2‐alkyl‐3‐hydroxyalkanoic acids. We now show that the final step in the pathway is an OleC‐catalyzed ATP‐dependent decarboxylative dehydration to form the corresponding Z olefins. Higher k cat /K m values were seen for substrates with longer alkyl chains. All four stereoisomers of 2‐hexyl‐3‐hydroxydecanoic acid were shown to be substrates, and GC‐MS and NMR analyses confirmed that the product in each case was ( Z )‐pentadec‐7‐ene. LC‐MS analysis supported the formation of AMP adduct as an intermediate. The enzymatic and stereochemical course of olefin biosynthesis from long‐chain fatty acids by OleA, OleD and OleC is now established.
Type of Medium:
Online Resource
ISSN:
1439-4227
,
1439-7633
DOI:
10.1002/cbic.201600063
Language:
English
Publisher:
Wiley
Publication Date:
2016
detail.hit.zdb_id:
2020469-3
SSG:
12
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