Isolation and structure elucidation of tumescenamides A and B, two peptides produced by Streptomyces tumescens YM23-260.
Two peptides, tumescenamides A and B, were isolated from the fermentation broth of a marine bacterium, Streptomyces tumescens YM23-260. The structure of tumescenamide A was determined to be a cyclic depsipeptide consisting of α-amino-2-butenoic acid, tyrosine, valine, leucine and threonine, substituted with a 2,4-dimethylheptanoyl residue at the α-NH(2) position. Tumescenamide B possesses a 2,4,6-trimethylnonanoyl residue in place of the 2,4-dimethylheptanoyl substituent in tumescenamide A. Tumescenamide A induced reporter gene expression under the control of the insulin-degrading enzyme promoter.
Motohashi
Keiichiro
K
Bioregulatory Lab, Faculty of Applied Bioscience, Tokyo University of Agriculture, Setagaya-ku, Tokyo, Japan.
Toda
Takashi
T
Sue
Masayuki
M
Furihata
Kazuo
K
Shizuri
Yoshikazu
Y
Matsuo
Yoshihide
Y
Kasai
Hiroaki
H
Shin-ya
Kazuo
K
Takagi
Motoki
M
Izumikawa
Miho
M
Horikawa
Yukio
Y
Seto
Haruo
H
D000596:Amino Acids / Q000032:analysis; D047630:Depsipeptides / Q000737:chemistry* / Q000302:isolation & purification* / Q000378:metabolism / Q000494:pharmacology; D017930:Genes, Reporter; D007339:Insulysin / Q000096:biosynthesis / Q000235:genetics; D008156:Luciferases / Q000096:biosynthesis / Q000235:genetics; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011401:Promoter Regions, Genetic; D013302:Streptomyces / Q000378:metabolism*; D015533:Transcriptional Activation
D000596:Amino Acids; D047630:Depsipeptides; D008156:Luciferases; D007339:Insulysin