937
Views
6
CrossRef citations to date
0
Altmetric
Research Article

The synthesis and biological activity of lipophilic derivatives of bicine conjugated with N3-(4-methoxyfumaroyl)-L-2,3-diaminopropanoic acid (FMDP)—an inhibitor of glucosamine-6-phosphate synthase

, , &
Pages 167-173 | Received 23 Nov 2010, Accepted 13 Apr 2011, Published online: 03 Jun 2011

References

  • Sundriyal S, Sharma RK, Jain R. Current advances in antifungal targets and drug development. Curr Med Chem 2006;13:1321–1335.
  • Andriole TA. Current and future antifungal therapy: new targets for antifungal agents. J Antimicrob Chemother 1999;44:151–162.
  • Milewski S. Glucosamine-6-phosphate synthase—the multi-facets enzyme. Biochim Biophys Acta 2002;1597:173–192.
  • Chmara H, Smulkowski M, Borowski E. Growth inhibitory effect of amidotransferase inhibition in Candida albicans by epoxy-peptides. Drugs Under Exptl Clin Res 1980;6:7–14.
  • Milewski S, Chmara H, Borowski E. Antibiotic tetaine—a selective inhibitor of chitin and mannoprotein biosynthesis in Candida albicans. Arch Microbiol 1986;145:234–240.
  • Badet B, Vermoote P, Le Goffic F. Glucosamine synthetase from Escherichia coli: kinetic mechanism and inhibition by N3-fumaroyl-l-2,3-diaminopropionic derivatives. Biochemistry 1988;27:2282–2287.
  • Bates CJ, Adams WR, Handschumacher RE. Control of the formation of uridine diphospho-N-acetyl-hexosamine and glycoprotein synthesis in rat liver. J Biol Chem 1966;241:1705–1712.
  • Borowski E. Novel approaches in the rational design of antifungal agents of low toxicity. Farmaco 2000;55:206–208.
  • Andruszkiewicz R, Chmara H, Milewski S, Kasprzak L, Borowski E. Structural determinants of inhibitory activity of N3-(4-methoxyfumaroyl)-l-2,3-diaminopropanoic acid towards glucosamine-6-phosphate synthase. Pol J Chem 1993;67:673–683.
  • Andruszkiewicz R, Chmara H, Milewski S, Borowski E. Synthesis of N3-fumaramoyl-l-2,3-diaminopropanoic acid analogues, the irreversible inhibitors of glucosamine synthetase. Int J Pept Protein Res 1986;27:449–453.
  • Clayton JP, Cole M, Elson SW, Ferres H, Hanson JC, Mizen LW et al. Preparation, hydrolysis, and oral absorption of lactonyl esters of penicillins. J Med Chem 1976;19:1385–1391.
  • Daehne W, Frederiksen E, Gundersen E, Lund F, Morch P, Petersen HJ et al. Acyloxymethyl esters of ampicillin. J Med Chem 1970;13:607–612.
  • Greenwald RB, Zhao H, Yang K, Reddy P, Martinez A. A new aliphatic amino prodrug system for the delivery of small molecules and proteins utilizing novel PEG derivatives. J Med Chem 2004;47:726–734.
  • Suggs JW, Pires RM. Facile hydrolysis and formation of amide bonds by N-hydroxyethylation of α-amino acids. Tetrahedron Lett 1997;38:2227–2230.
  • Andruszkiewicz R, Koszel D. A simple access to O-acyl bicine. Pol J Chem 2007;81:295–298.
  • Ong S, Liu H, Pidgeon C. Immobilized-artificial-membrane chromatography: measurements of membrane partition coefficient and predicting drug membrane permeability. J Chromatogr A 1996;728:113–128.
  • Hassner A, Alexanian V. Direct room temperature esterification of carboxylic acids. Tetrahedron Lett 1978;46:4475–4478.
  • Ulich LH, Adams R. The reaction between acid halides and aldehydes. J Am Chem Soc 1921;43:660–667.
  • Ono N, Yamada T, Saito T, Tanaka K, Kaji A. A convenient procedure for esterification of carboxylic acids. Bull Chem Soc JPN 1978;51:2401–2404.
  • Anderson GW, Zimmerman JE, Callahan FM. The use of esters of N-hydroxysuccinimide in peptide synthesis. J Am Chem Soc 1964;86:1839–1842.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.