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  • Title: Studies on steroids. CCLIII. Capillary gas chromatographic behaviour of diethylhydrogensilyl-diethylsilylene derivatives of stereoisomeric bile acids.
    Author: Goto J, Teraya Y, Nambara T, Iida T.
    Journal: J Chromatogr; 1991 Nov 01; 585(2):281-8. PubMed ID: 1804843.
    Abstract:
    The capillary gas chromatographic behaviour of diethylhydrogensilyl (DEHS) ethers and/or diethylsilylene (DES) derivatives of fifty bile acids including 4- and 6-hydroxylated compounds is described. The methylene unit (MU) values of methyl and pentafluorobenzyl esters of bile acids were determined as their trimethylsilyl (TMS), dimethylethylsilyl (DMES) ethers and DEHS-DES derivatives. The differences in methylene unit values between the corresponding TMS ethers and DMES ethers or DEHS-DES derivatives were used for estimating the number and stereochemistry of hydroxyl groups on the steroid nucleus. On treatment with the silylating agent N,O-bis (diethylhydrogensilyl)trifluoroacetamide, bile acids possessing isolated hydroxyl in addition to diaxial trans-glycol groups were easily converted into the DEHS ehters, whereas those having a vicinal glycol group except for the diaxial group were converted into cyclic DES derivatives. The mass spectrometric properties obtained with negative-ion chemical ionization detection are discussed.
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