Anticandidal properties of N3-(4-methoxyfumaroyl)-L-2,3-diaminopropanoic acid oligopeptides
- PMID: 2104933
- DOI: 10.1021/jm00163a022
Anticandidal properties of N3-(4-methoxyfumaroyl)-L-2,3-diaminopropanoic acid oligopeptides
Abstract
Tri-, tetra-, and pentapeptides containing N3-(4-methoxyfumaroyl)-L-2,3-diaminopropanoic acid (FMDP), an inactivator of glucosamine 6-phosphate synthase of fungal origin (a key enzyme in the biosynthesis of macromolecular components of the fungal cell wall) have been synthesized and investigated as anticandidal agents. Structure-activity relationships of a series of peptides revealed that tripeptides were generally more active than the other peptides examined. In this study, the lysyl peptide, Lys-Nva-FMDP has been found to be the most active compound in the series.
Similar articles
-
Antifungal peptides with novel specific inhibitors of glucosamine 6-phosphate synthase.Drugs Exp Clin Res. 1988;14(7):461-5. Drugs Exp Clin Res. 1988. PMID: 3149235
-
Synthesis, anticandidal activity of N(3)-(4-methoxyfumaroyl)-(S)-2,3-diaminopropanoic amide derivatives--novel inhibitors of glucosamine-6-phosphate synthase.Eur J Med Chem. 2015 Jan 27;90:577-82. doi: 10.1016/j.ejmech.2014.12.007. Epub 2014 Dec 5. Eur J Med Chem. 2015. PMID: 25497131
-
Amide and ester derivatives of N3-(4-methoxyfumaroyl)-(S)-2,3-diaminopropanoic acid: the selective inhibitor of glucosamine-6-phosphate synthase.Bioorg Med Chem. 2001 Apr;9(4):931-8. doi: 10.1016/s0968-0896(00)00315-1. Bioorg Med Chem. 2001. PMID: 11354676
-
Glucosamine-6-phosphate synthase, a novel target for antifungal agents. Molecular modelling studies in drug design.Acta Biochim Pol. 2005;52(3):647-53. Epub 2005 Aug 4. Acta Biochim Pol. 2005. PMID: 16082410 Review.
-
Glucosamine-6-phosphate synthase--the multi-facets enzyme.Biochim Biophys Acta. 2002 Jun 3;1597(2):173-92. doi: 10.1016/s0167-4838(02)00318-7. Biochim Biophys Acta. 2002. PMID: 12044898 Review.
Cited by
-
Inhibitors of glucosamine-6-phosphate synthase as potential antimicrobials or antidiabetics - synthesis and properties.J Enzyme Inhib Med Chem. 2022 Dec;37(1):1928-1956. doi: 10.1080/14756366.2022.2096018. J Enzyme Inhib Med Chem. 2022. PMID: 35801410 Free PMC article.
-
Enhanced susceptibility to antifungal oligopeptides in yeast strains overexpressing ABC multidrug efflux pumps.Antimicrob Agents Chemother. 2008 Nov;52(11):4057-63. doi: 10.1128/AAC.01648-07. Epub 2008 Sep 15. Antimicrob Agents Chemother. 2008. PMID: 18794383 Free PMC article.
-
Transport Deficiency Is the Molecular Basis of Candida albicans Resistance to Antifungal Oligopeptides.Front Microbiol. 2017 Nov 7;8:2154. doi: 10.3389/fmicb.2017.02154. eCollection 2017. Front Microbiol. 2017. PMID: 29163437 Free PMC article.
-
A theoretical study of glucosamine synthase. II. Combined quantum and molecular mechanics simulation of sulfhydryl attack on the carboxyamide group.Eur Biophys J. 1992;21(2):137-45. doi: 10.1007/BF00185428. Eur Biophys J. 1992. PMID: 1396403
-
Investigation of the inhibition pathway of glucosamine synthase by N3-(4-methoxyfumaroyl)-L-2,3-diaminopropanoic acid by semiempirical quantum mechanical and molecular mechanics methods.Eur Biophys J. 1992;21(4):273-80. doi: 10.1007/BF00185122. Eur Biophys J. 1992. PMID: 1425480
Publication types
MeSH terms
Substances
LinkOut - more resources
Other Literature Sources