Asymmetric synthesis of diastereomeric diaminoheptanetetraols. A proposal for the configuration of (+)-zwittermicin a.
[structure: see text] 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.
Rogers
Evan W
EW
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093, USA.
Molinski
Tadeusz F
TF
D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D001409:Bacillus cereus / Q000737:chemistry*; D018360:Crystallography, X-Ray; D019850:Heptanol / Q000031:analogs & derivatives; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D010455:Peptides / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D010455:Peptides; C088290:zwittermicin A; D019850:Heptanol