Document Detail

UDPglucose: fatty acid transglucosylation and transacylation in triacylglucose biosynthesis.
MedLine Citation:
PMID:  11607435     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Glandular trichomes of the wild tomato Lycopersicon pennellii Corr. (D'Arcy) secrete large amounts of 2,3,4-tri-O-acylglucoses possessing straight- and branched-chain fatty acids of short to medium chain length (C4-C12). Although previous biosynthetic studies suggested that glucose acylation proceeded via acyl CoA intermediates, repeated attempts to demonstrate isobutyryl-CoA-dependent glucose acylation were unsuccessful. When [14C]isobutyrate is administered to detached L. pennellii leaves, the label is readily converted to 1-O-isobutyryl-beta-D-glucose. This is immediately followed by the appearance of di- and triacylated glucose esters. L. pennellii extracts catalyzed the formation of 1-O-isobutyryl-beta-D-glucose from isobutyrate and UDPglucose, and detached L. pennellii trichomes catalyzed transfer of the isobutyryl moiety from synthetic 1-O-isobutyryl-beta-D-glucose to D-glucose. Detached L. pennellii trichomes also catalyzed the formation of diacylglucose and triacylglucose via transfer of the isobutyryl moiety from 1-O-[14C]isobutyryl-beta-D-glucose to mono- or diacylglucoses, respectively. These studies suggest a multistep mechanism in which activation of fatty acids to their respective high-energy 1-O-acyl-beta-D-glucopyranose derivatives is followed by transfer of the 1-O-acyl moiety to non-anomeric positions of other glucose and/or partially acylated glucose molecules. This appears to be the primary mechanism of activation and fatty acid esterification to glucose in L. pennellii trichomes. Cultivated tomato, L. esculentum Mill., also activates free fatty acids to their 1-O-acyl-beta-D-glucose derivatives but lacks the acyl transfer mechanism for synthesizing polyacylated sugars.
G S Ghangas; J C Steffens
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Proceedings of the National Academy of Sciences of the United States of America     Volume:  90     ISSN:  0027-8424     ISO Abbreviation:  Proc. Natl. Acad. Sci. U.S.A.     Publication Date:  1993 Nov 
Date Detail:
Created Date:  2001-10-18     Completed Date:  2001-12-07     Revised Date:  2010-09-14    
Medline Journal Info:
Nlm Unique ID:  7505876     Medline TA:  Proc Natl Acad Sci U S A     Country:  United States    
Other Details:
Languages:  eng     Pagination:  9911-5     Citation Subset:  -    
Department of Plant Breeding, Cornell University, Ithaca, NY 14853-1902, USA.
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