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J. Biochem, 1986, Vol. 99, No. 5 1339-1344
© 1986 Japanese Biochemical Society

research-article

Stereochemistry of 2,3-Alkanediols Obtained from the Harderian Gland of Mongolian Gerbil (Meriones unguiculatus)1

Hideaki OTSUKA*, Osamu OTSURU**, Takeshi KASAMA***, Akihiko KAWAGUCHI****, Kazuo YAMASAKI* and Yousuke SEYAMA***

*Department of Pharmacognosy, Institute of Pharmaceutical Sciences, Hiroshoima University School of Medicine Kasumi, Minami-ku, Hiroshima 734
**Identification Center, National Research Institute of Police Science Sanban-cho, Chiyoda-ku, Tokyo 102
***Department of Physiological Chemistry and Nutrition, Faculty of Medicine, The University of Tokyo Hongo, Bunkyo-ko, Tokyo 113
****Department of Biology, The University of Tokyo Komaba, Meguro-ku, Tokyo 153

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.

1This investigation was supported in part by a Grant-in-Aid from the Ministry of Education, Science and Culture of Japan.


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