The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Arylomycins A and B, New Biaryl-bridged Lipopeptide Antibiotics Produced by Streptomyces sp. Tü 6075
II. Structure Elucidation
ALEXANDRA HÖLTZELDIETMAR G. SCHMIDGRAEME J. NICHOLSONSTEFAN STEVANOVICJUDITH SCHIMANAKLAUS GEBHARDTHANS-PETER FIEDLERGÜNTHER JUNG
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2002 年 55 巻 6 号 p. 571-577

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The structures of new lipopeptide antibiotics, arylomycins A and B, were elucidated by a combination of ESI-FTICR-mass spectrometry, NMR spectroscopy, EDMAN sequencing, and fatty acid and chiral amino acid analyses. The colourless arylomycins A share the peptide sequence of D-N-methylseryl2(D-MeSer2)-D-alanyl3-glycyl4-N-methyl-4-hydroxyphenylglycyl5-(MeHpg5)-L-alanyl6-tyrosine7 cyclised by a [3, 3]biaryl bond between MeHpg5 and Tyr7. The yellow arylomycins B differ from arylomycins A by nitro substitution of Tyr7. The N-termini of arylomycins A and B are acylated with saturated C11-C15 fatty acids (fa1) comprising n, iso, and anteiso isomers. Arylomycins A and B represent the first examples of biaryl-bridged lipopeptides.

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