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

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 sp...

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Bibliographic Details
Published in:Journal of antibiotics 2004/01/25, Vol.57(1), pp.52-58
Main Authors: HASHIZUME, HIDEKI, HIROSAWA, SEHEI, SAWA, RYUICHI, MURAOKA, YASUHIKO, IKEDA, DAISHIRO, NAGANAWA, HIROSHI, IGARASHI, MASAYUKI
Format: Article
Language:English
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Summary: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.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.57.52