Arylomycins A and B, New Biaryl-bridged Lipopeptide Antibiotics Produced by Streptomyces sp. Tü 6075 II. Structure Elucidation

ALEXANDRA HÖLTZEL; DIETMAR G. SCHMID; GRAEME J. NICHOLSON; STEFAN STEVANOVIC; JUDITH SCHIMANA; KLAUS GEBHARDT; HANS-PETER FIEDLER; GÜNTHER JUNG

doi:10.7164/antibiotics.55.571

Arylomycins A and B, New Biaryl-bridged Lipopeptide Antibiotics Produced by Streptomyces sp. Tü 6075

II. Structure Elucidation

ALEXANDRA HÖLTZEL, DIETMAR G. SCHMID, GRAEME J. NICHOLSON, STEFAN STEVANOVIC, JUDITH SCHIMANA, KLAUS GEBHARDT, HANS-PETER FIEDLER, GÜNTHER JUNG

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JOURNAL FREE ACCESS

2002 Volume 55 Issue 6 Pages 571-577

DOI https://doi.org/10.7164/antibiotics.55.571

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Abstract

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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