Structure and absolute stereochemistry of 21-hydroxyoligomycin A.
21-Hydroxyoligomycin A (1) was isolated from Streptomyces cyaneogriseus ssp. noncyanogenus (LL-F28249) and fully characterized by NMR and single-crystal X-ray diffraction methods. The complete 1H and 13C NMR chemical shift assignments for 1 were made using 2D NMR experiments, and the chirality at C-21 was deduced to be R from a J-based configuration analysis. The absolute configuration at C-21 and at the other 18 chiral centers in the molecule were independently confirmed by anomalous dispersion measurements on a crystal of the chloroform methanol solvate of 21-hydroxyoligomycin A (1).
Wagenaar
Melissa M
MM
Wyeth Research, 401 N. Middletown Road, Pearl River, NY 10965, USA. wagenam@wyeth.com
Williamson
R Thomas
RT
Ho
Douglas M
DM
Carter
Guy T
GT
D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009840:Oligomycins / Q000737:chemistry*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry*
D009840:Oligomycins; C072367:21-hydroxyoligomycin A