Himastatin, a New Antitumor Antibiotic from Streptomyces hygroscopicus III. Structural Elucidation

JOHN E. LEET; DANIEL R. SCHROEDER; JERZY GOLIK; JAMES A. MATSON; TERRENCE W. DOYLE; KIN S. LAM; SUSAN E. HILL; MIKE S. LEE; JEFFREY L. WHITNEY; BALA S. KRISHNAN

doi:10.7164/antibiotics.49.299

Himastatin, a New Antitumor Antibiotic from Streptomyces hygroscopicus

III. Structural Elucidation

JOHN E. LEET, DANIEL R. SCHROEDER, JERZY GOLIK, JAMES A. MATSON, TERRENCE W. DOYLE, KIN S. LAM, SUSAN E. HILL, MIKE S. LEE, JEFFREY L. WHITNEY, BALA S. KRISHNAN

Author information

JOHN E. LEET
Bristol-Myers Squibb Pharmaceutical Research Institute
DANIEL R. SCHROEDER
Bristol-Myers Squibb Pharmaceutical Research Institute
JERZY GOLIK
Bristol-Myers Squibb Pharmaceutical Research Institute
JAMES A. MATSON
Bristol-Myers Squibb Pharmaceutical Research Institute
TERRENCE W. DOYLE
Bristol-Myers Squibb Pharmaceutical Research Institute
KIN S. LAM
Bristol-Myers Squibb Pharmaceutical Research Institute
SUSAN E. HILL
Bristol-Myers Squibb Pharmaceutical Research Institute
MIKE S. LEE
Bristol-Myers Squibb Pharmaceutical Research Institute
JEFFREY L. WHITNEY
Bristol-Myers Squibb Pharmaceutical Research Institute
BALA S. KRISHNAN
Bristol-Myers Squibb Pharmaceutical Research Institute

JOURNAL FREE ACCESS

1996 Volume 49 Issue 3 Pages 299-311

DOI https://doi.org/10.7164/antibiotics.49.299

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Abstract

The structure of the antitumor antibiotic himastatin was determined using a combination of spectroscopic and chemical degradation techniques. Himastatin is a unique dimeric cyclohexadepsipeptide joined through a biphenyl linkage between two oxidized tryptophan units. The gross structure of the dimer was established through degradative ozonolysis. Himastatin consists of D-valine, D-threonine, L-leucine, L-α-hydroxyisovaleric acid, (3R, 5R)-5-hydroxypiperazic acid, and (2R, 3aR, 8aR)-3a-hydroxyhexahydropyrrolo[2, 3b]indole 2-carboxylic acid subunits.

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