Nuclear Magnetic Resonance and Biosynthetic Studies of Neoantimycin and Structure Elucidation of Isoneoantimycin, a Minor Metabolite Related to Neoantimycin

In preparation for biosynthetic studies on the 3,4-dihydroxy-2,6-dimethyl-5-phenylvaleric acid portion of neoantimycin (1), the 1H and 13C NMR signals of 1 were assigned unambiguously by means of 2D correlation spectroscopy and NOE experiments. The previously undetermined absolute stereochemistry at...

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Bibliographic Details
Published in:	Journal of natural products (Washington, D.C.) Vol. 61; no. 8; pp. 978 - 981
Main Authors:	Takeda, Yoshio, Masuda, Toshiya, Matsumoto, Takashi, Takechi, Yuusuke, Shingu, Tetsuro, Floss, Heinz G
Format:	Journal Article
Language:	English
Published:	Washington, DC American Chemical Society 01-08-1998 Glendale, AZ American Society of Pharmacognosy
Subjects:	Anti-Bacterial Agents - biosynthesis Anti-Bacterial Agents - chemistry antimycin A Bacteriology biochemical pathways Biological and medical sciences biosynthesis Biotransformation chemical reactions chemical structure Culture Media Fundamental and applied biological sciences. Psychology Isomerism Magnetic Resonance Spectroscopy metabolites Microbiology Morphology, structure, chemical composition Organic Chemicals precursors spectral analysis Spectrophotometry, Infrared Spectrophotometry, Ultraviolet Streptomyces Streptomyces - metabolism Streptomycetaceae Hydroxyester Streptomyces fradiae Metabolite Lactone Ring cleavage Macrocycle Actinomycetales α-Aminoacid Antibiotic Microbial origin Bacteria S configuration Isolation Actinomycetes Structural analysis
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Summary:	In preparation for biosynthetic studies on the 3,4-dihydroxy-2,6-dimethyl-5-phenylvaleric acid portion of neoantimycin (1), the 1H and 13C NMR signals of 1 were assigned unambiguously by means of 2D correlation spectroscopy and NOE experiments. The previously undetermined absolute stereochemistry at C-15 and C-16 was deduced as (S) and (S). The structure of isoneoantimycin (2) was also elucidated. The methyl groups of methionine and propionate were incorporated stereospecifically into C-13 and C-12 of 1, respectively, and the configuration of the methyl group of methionine is inverted in the process. The results also suggest the intervention of phenylpyruvate as an actual precursor.
Bibliography:	ark:/67375/TPS-F01ZDR8X-R istex:0A67C198E8E6ABDF4A0D76DAF30E35D602EA0EF3 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0163-3864 1520-6025
DOI:	10.1021/np9800194