Stereochemistry of 2,3-alkanediols obtained from the Harderian gland of Mongolian gerbil (Meriones unguiculatus).
The stereochemistry of the alcohol moieties of 2,3-alkanediol diacyl esters obtained from the Harderian gland of the Mongolian gerbil was investigated. There were five major 2,3-alkanediols, C14-C22 (even carbon numbers), all having the erythro configuration as determined by GC-MS analysis of their isopropylidene derivatives in comparison with synthetic erythro- and threo-2,3-hexadecanediols. 13C-NMR spectroscopy of the synthetic materials showed distinct differences of chemical shift at the C-1, C-3, and C-4 carbons, from which the native 2,3-alkanediols were definitely determined to be in the erythro series. The absolute configurations of the C-2 and C-3 asymmetric centers were assigned as 2S and 3R, respectively, based on known 2S,3R-octanediol.
H
H
Otsuka
O
O
Otsuru
T
T
Kasama
A
A
Kawaguchi
K
K
Yamasaki
Y
Y
Seyama
D000818:Animals; D005233:Fatty Alcohols / Q000302:isolation & purification*; D008401:Gas Chromatography-Mass Spectrometry; D005849:Gerbillinae; D006243:Harderian Gland / Q000032:analysis*; D007765:Lacrimal Apparatus / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation
D005233:Fatty Alcohols