THE STRUCTURES OF KATANOSINS A AND B

1H and 13C NMR studies on katanosin A confirmed the presence of eight usual amino acid residues which were previously deduced by amino acid analysis and suggested the presence of β-hydroxyaspartic acid, β-hydroxyleucine and β-phenylserine residues. These amino acids were isolated and confirmed, incl...

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Bibliographic Details
Published in:Journal of antibiotics 1988/06/25, Vol.41(6), pp.719-725
Main Authors: KATO, TOSHIYUKI, HINOO, HIROSHI, TERUI, YOSHIHIRO, KIKUCHI, JUN'KO, SHOJI, JUN'ICHI
Format: Article
Language:English
Subjects:
Amino Acid Sequence
Amino Acids - analysis
Anti-Bacterial Agents - analysis
Biological and medical sciences
Chemical Phenomena
Chemistry
Depsipeptides
General pharmacology
Medical sciences
Peptides - analysis
Pharmacology. Drug treatments
Physicochemical properties. Structure-activity relationships
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Summary:1H and 13C NMR studies on katanosin A confirmed the presence of eight usual amino acid residues which were previously deduced by amino acid analysis and suggested the presence of β-hydroxyaspartic acid, β-hydroxyleucine and β-phenylserine residues. These amino acids were isolated and confirmed, including their stereochemistries, by comparison with the respective authentic specimens. Stereochemistries of the usual amino acids were determined by comparing the L-leucylated amino acids with reference compounds by HPLC. Lithium borohydride reduction and chromic acid oxidation of katanosin A and alkali-treated katanosin A elucidated a lactone linkage between the C-terminal Ser and phenylserine residues. Edman degradation on alkali-treated katanosin A clarified the total amino acid sequence. The difference in katanosins A and B was determined to be replacement of Val in A by He in B. Thus, the structures of katanosins A and B were elucidated.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.41.719