Asymmetric Synthesis of Diastereomeric Diaminoheptanetetraols. A Proposal for the Configuration of (+)-Zwittermicin A

A proposed absolute configuration for the 7 stereocenters in (+)-zwittermicin A is described based on asymmetric synthesis of six diastereomeric 2,6-diamino-1,3,5,7-heptanetetraols corresponding to the C9−C15 segment, pairwise 13C NMR chemical shift difference analysis of the models with the natural...

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Bibliographic Details
Published in:Organic letters 2007-02, Vol.9 (3), p.437-440
Main Authors: Rogers, Evan W, Molinski, Tadeusz F
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - pharmacology
Bacillus cereus - chemistry
Crystallography, X-Ray
Heptanol - analogs & derivatives
Magnetic Resonance Spectroscopy
Models, Chemical
Peptides - chemistry
Peptides - pharmacology
Stereoisomerism
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Summary:A proposed absolute configuration for the 7 stereocenters in (+)-zwittermicin A is described based on asymmetric synthesis of six diastereomeric 2,6-diamino-1,3,5,7-heptanetetraols corresponding to the C9−C15 segment, pairwise 13C NMR chemical shift difference analysis of the models with the natural product, interpretation of enantiospecificity of the serine loading domain of the zwittermicin A biosynthetic gene cluster, and degradation of the natural product.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol062804a