The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Argyrins, Immunosuppressive Cyclic Peptides from Myxobacteria
II. Structure Elucidation and Stereochemistry
LARISSA VOLLBRECHTHEINRICH STEINMETZGERHARD HÖFLELUKAS OBERERGRETY RIHSGÜNTER BOVERMANNPETER VON MATT
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2002 Volume 55 Issue 8 Pages 715-721

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Abstract

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 α-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.

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