Arylomycins A and B, new biaryl-bridged lipopeptide antibiotics produced by Streptomyces sp. Tü 6075. II. Structure elucidation.
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.
Institut fur Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, D-72076 Tübingen, Germany.
Alexandra
A
Höltzel
Dietmar G
DG
Schmid
Graeme J
GJ
Nicholson
Stefan
S
Stevanovic
Judith
J
Schimana
Klaus
K
Gebhardt
Hans-Peter
HP
Fiedler
Günther
G
Jung
D000596:Amino Acids / Q000032:analysis; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000302:isolation & purification; D005227:Fatty Acids / Q000032:analysis; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D010456:Peptides, Cyclic / Q000737:chemistry* / Q000302:isolation & purification; D020539:Sequence Analysis, Protein; D013302:Streptomyces / Q000737:chemistry*
D000596:Amino Acids; D000900:Anti-Bacterial Agents; D005227:Fatty Acids; D010456:Peptides, Cyclic