An efficient synthesis of argifin: A natural product chitinase inhibitor with chemotherapeutic potential

The first synthesis of the cyclopentapeptide family 18 chitinase inhibitor argifin has been achieved by a combination of solid phase and solution chemistry. Synthetic argifin is a nanomolar inhibitor of chitinase B1 from Aspergillus fumigatus and the high-resolution X-ray structure of the synthesize...

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Veröffentlicht in:	Bioorganic & medicinal chemistry letters 2005-11, Vol.15 (21), p.4717-4721
Hauptverfasser:	Dixon, Mark J., Andersen, Ole A., van Aalten, Daan M.F., Eggleston, Ian M.
Format:	Artikel
Sprache:	eng
Schlagworte:	Analytical, structural and metabolic biochemistry Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Aspergillus fumigatus - enzymology Biological and medical sciences Biological Products - chemical synthesis Biological Products - chemistry Chitinase inhibitor Chitinases - antagonists & inhibitors Chitinases - chemistry Crystallography, X-Ray Cyclic peptide Enzymes and enzyme inhibitors Fundamental and applied biological sciences. Psychology Hydrolases Kinetics Medical sciences Miscellaneous Models, Molecular Natural product Peptides, Cyclic - chemical synthesis Peptides, Cyclic - chemistry Pharmacology. Drug treatments Solid phase synthesis Structure-Activity Relationship
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Beschreibung
Zusammenfassung:	The first synthesis of the cyclopentapeptide family 18 chitinase inhibitor argifin has been achieved by a combination of solid phase and solution chemistry. Synthetic argifin is a nanomolar inhibitor of chitinase B1 from Aspergillus fumigatus and the high-resolution X-ray structure of the synthesized material in complex with the same enzyme is identical to that previously obtained for the natural product.
ISSN:	0960-894X 1464-3405
DOI:	10.1016/j.bmcl.2005.07.068