Document Detail

Probing the stereochemistry of E. coli 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase (phenylalanine-sensitive)-catalyzed synthesis of KDO 8-P analogues.
MedLine Citation:
PMID:  10987918     Owner:  NLM     Status:  MEDLINE    
The five-carbon phosphorylated monosaccharide analogues, D-arabinose 5-phosphate, D-ribose 5-phosphate, and 2-deoxy-D-ribose 5-phosphate, were separately condensed with (Z)- and (E)-[3-(2)H]-phosphoenolpyruvate (PEP) in the presence of Escherichia coli 3-deoxy-D-arabino-heptulosonate 7-phosphate (DAH 7-P) synthase (phe) to give in the case of (Z)-[3-(2)H]-PEP (3S)-[3-(2)H]-3-deoxy-D-manno-octulosonate 8-phosphate, (3S)-[3-(2)H]-3-deoxy-D-altro-octulosonate 8-phosphate, and (3S)-[3-(2)H]-3,5-dideoxy-D-altro-octulosonate 8-phosphate, respectively, whereas incubation with (E)-[3-(2)H]-PEP gives the corresponding (3R)-monosaccharides. These results are in complete agreement with the observed facial selectivity of DAH 7-P synthase for its normal substrates D-erythrose 4-phosphate and PEP and provide direct evidence that DAH 7-P synthase (phe) catalyzes the si face addition of the C3 of PEP to the re face of C1 of the phosphorylated monosaccharides tested. Products formed by DAH 7-P synthase (phe)-catalyzed condensation of (Z)- and (E)-[3-F]-PEP with E 4-P were completely characterized by (1)H and (19)F NMR analysis for the first time. Results of our studies suggest that disappearence of the double bond between C2 and C3 of PEP and formation of a bond between C3 of PEP and C1 of the phosphorylated monosaccharide tested occur in concert during the DAH 7-P synthase-catalyzed condensation reaction.
A K Sundaram; R W Woodard
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  65     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2000 Sep 
Date Detail:
Created Date:  2000-11-07     Completed Date:  2000-11-07     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  5891-7     Citation Subset:  IM    
Interdepartmental Program in Medicinal Chemistry, College of Pharmacy, University of Michigan, Ann Arbor, Michigan 48109-1065, USA.
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MeSH Terms
3-Deoxy-7-Phosphoheptulonate Synthase / chemistry*
Escherichia coli / chemistry*
Magnetic Resonance Spectroscopy
Molecular Conformation
Phenylalanine / chemistry*
Sugar Acids / chemical synthesis*,  chemistry,  isolation & purification
Sugar Phosphates / chemical synthesis*,  chemistry,  isolation & purification
Grant Support
Reg. No./Substance:
0/3-deoxyoctulosonate 8-phosphate; 0/Sugar Acids; 0/Sugar Phosphates; 63-91-2/Phenylalanine; EC Synthase

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