Argyrins, immunosuppressive cyclic peptides from myxobacteria. II. Structure elucidation and stereochemistry

The structures of argyrins A-H were elucidated by NMR spectroscopy, chemical degradation and X-ray analysis as cyclic octapeptides. Argyrins A and B, in addition to the common amino acids tryptophan, glycine, dehydroalanine and alanine or alpha-aminobutyric acid, sarcosine, contain 2-(1-aminoethyl)t...

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Bibliographic Details
Published in:	Journal of antibiotics Vol. 55; no. 8; p. 715
Main Authors:	Vollbrecht, Larissa, Steinmetz, Heinrich, Hofle, Gerhard, Oberer, Lukas, Rihs, Grety, Bovermann, Günter, von Matt, Peter
Format:	Journal Article
Language:	English
Published:	Japan 01-08-2002
Subjects:	Crystallography, X-Ray Immunosuppressive Agents - chemistry Magnetic Resonance Spectroscopy Molecular Conformation Myxococcales - metabolism Peptides, Cyclic - chemistry
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Summary:	The structures of argyrins A-H were elucidated by NMR spectroscopy, chemical degradation and X-ray analysis as cyclic octapeptides. Argyrins A and B, in addition to the common amino acids tryptophan, glycine, dehydroalanine and alanine or alpha-aminobutyric acid, sarcosine, contain 2-(1-aminoethyl)thiazol-4-caboxylic acid and the novel amino acid 4'-methoxytryptophan. In argyrins C and D the latter is replaced by 4'-methoxy 2'-methyltryptophan. According to NMR analysis the solution and crystal conformations of argyrins A and B are identical in CDCl3 and slightly different in acetone-d6. Argyrins A and B are identical with the antibiotics A21459 A and B, whose structures are revised with respect to 4'-methoxytryptophan.
ISSN:	0021-8820
DOI:	10.7164/antibiotics.55.715