Document Detail

Synthesis of N3-fumaramoyl-L-2,3-diaminopropanoic acid analogues, the irreversible inhibitors of glucosamine synthetase.
MedLine Citation:
PMID:  3089958     Owner:  NLM     Status:  MEDLINE    
Several analogues of N3-fumaramoyl-L-2,3-diaminopropanoic acid were synthesized and evaluated for inhibition of glucosamine-6-phosphate synthetase activity. The syntheses were accomplished by acylation reaction of N2-tert.-butoxycarbonyl-L-2,3-diaminopropanoic acid (Boc-A2pr) or N2-tert.-butoxycarbonyl-L-2,4-diaminobutanoic acid (Boc-A2-bu) with the N-succinimidoyl esters of several derivatives of alpha, beta-unsaturated acids 2a-d followed by deprotection of the Boc groups. The obtained compounds were tested for inhibition of glucosamine synthetase isolated from Salmonella typhimurium and Saccharomyces cerevisiae. The results indicated that among the synthesized compounds, N3-4-methoxyfumaroyl-L-2,3-diaminopropanoic acid (FMDP) was the most powerful inhibitor of glucosamine synthetase.
R Andruszkiewicz; H Chmara; S Milewski; E Borowski
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Publication Detail:
Type:  Comparative Study; Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  International journal of peptide and protein research     Volume:  27     ISSN:  0367-8377     ISO Abbreviation:  Int. J. Pept. Protein Res.     Publication Date:  1986 May 
Date Detail:
Created Date:  1986-09-16     Completed Date:  1986-09-16     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0330420     Medline TA:  Int J Pept Protein Res     Country:  DENMARK    
Other Details:
Languages:  eng     Pagination:  449-53     Citation Subset:  IM    
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MeSH Terms
Alanine / analogs & derivatives*
Fumarates / chemical synthesis*
Glutamine-Fructose-6-Phosphate Transaminase (Isomerizing) / antagonists & inhibitors*
Indicators and Reagents
Magnetic Resonance Spectroscopy
Saccharomyces cerevisiae / enzymology
Salmonella typhimurium / enzymology
Structure-Activity Relationship
Transaminases / antagonists & inhibitors*
beta-Alanine / analogs & derivatives*,  chemical synthesis
Reg. No./Substance:
0/Fumarates; 0/Indicators and Reagents; 107-95-9/beta-Alanine; 56-41-7/Alanine; EC 2.6.1.-/Transaminases; EC Transaminase (Isomerizing)

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