Tripropeptins, Novel Antimicrobial Agents Produced by Lysobacter sp. II. Structure Elucidation

HIDEKI HASHIZUME; SEHEI HIROSAWA; RYUICHI SAWA; YASUHIKO MURAOKA; DAISHIRO IKEDA; HIROSHI NAGANAWA; MASAYUKI IGARASHI

doi:10.7164/antibiotics.57.52

Tripropeptins, Novel Antimicrobial Agents Produced by Lysobacter sp.

II. Structure Elucidation

HIDEKI HASHIZUME, SEHEI HIROSAWA, RYUICHI SAWA, YASUHIKO MURAOKA, DAISHIRO IKEDA, HIROSHI NAGANAWA, MASAYUKI IGARASHI

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JOURNAL FREE ACCESS

2004 Volume 57 Issue 1 Pages 52-58

DOI https://doi.org/10.7164/antibiotics.57.52

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Abstract

Planar structures of tripropeptins (TPPs) were elucidated by spectroscopic studies including various NMR measurements. Stereochemistry of constituent amino acids of tripropeptin C (TPPC) (3) was identified by marfey's method except hydroxyproline which was determined by studies of NMR and CD spectra. The absolute structure of 3 was determined by analyses of the fragments obtained by Birch reduction and LiBH₄ reduction of 3. The configuration of the fatty acid, isolated from acid hydrolysate of 3, was determined to be (3R)-hydroxy-13-methyltetradecanoic acid from MS, NMR spectra and negative sign of the optical rotation.

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