Streptocidinis A similar to D, novel cyclic decapeptide antibiotics produced by Streptomyces sp Tu 6071 II. Structure elucidation

Citation
A. Holtzel et al., Streptocidinis A similar to D, novel cyclic decapeptide antibiotics produced by Streptomyces sp Tu 6071 II. Structure elucidation, J ANTIBIOT, 54(5), 2001, pp. 434-440
Citations number
9
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Microbiology
Journal title
JOURNAL OF ANTIBIOTICS
ISSN journal
0021-8820 → ACNP
Volume
54
Issue
5
Year of publication
2001
Pages
434 - 440
Database
ISI
SICI code
0021-8820(200105)54:5<434:SASTDN>2.0.ZU;2-2
Abstract
The structures of the new antibiotics streptocidins A-D were elucidated as cyclic decapeptides cyclo[L-Va1(1)-L-Om(2)-L-Leu(3)-D-Phe(4)-L-Pro(5)-L-Leu (6)-X-7-Leu-L-Asn(8)-L-Gln(9)-X-10] with X-7=D-Trp (A, B, C) Or D-Phe (D) a nd X-10=L-Tyr (A), L-Trp (B, D), or D-Trp (C). The amino acid composition ( including the configuration) of the substances was determined by chiral-pha se GC-MS of the hydrolysates. The sequences were established by EDMAN degra dation following linearisation of the cyclic peptides upon treatment with L iAlH4. NMR spectroscopic studies of streptocidins C and D confirmed the pro posed sequences and provided conformational data which indicate a molecular topology of streptocidins C and D similar to those of tyrocidine A and gra micidin S.