Gene/Protein Disease Symptom Drug Enzyme Compound
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Query: UMLS:C0338671 (Steroids)
 9,479 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

E-2,2,3',3'',5,5,5',5''-octadeuteriodiethylstilbestrol (DES-d8) and Z-2,3'3'',4,5,5,5',5''-octadeuterio-3,4-bis(p-hydroxyphenyl)-2-hexene (psi-DES-d8) were synthesized from E-diethylstilbestrol (DES) by hydrogen/deuterium exchange in a mixture of methanol-d and deuterium chloride in deuterium oxide. The structures, isotopic purity, and positions of uptake of deuterium were determined by nuclear magnetic resonance (NMR) and mass spectrometry (MS). Additional confirmation of the positions of deuterium exchange in stilbestrols was obtained from an analysis of the oxidation of dES-d8 to Z,Z-2,3',3'',5,5',5''-hexadeuteriodienestrol (beta-DIES-d6) and of the hydrogen/deuterium exchange reaction of hexestrol (HEX) to 3',3'',5',5''-hexestrol, (HEX-d4). Structural analysis and the determination of isotopic purity of the latter two compounds were also carried out by NMR and MS. The uptake of eight deuterium atoms by DES is postulated to proceed via two different reactions occurring simultaneously: 1. acid catalyzed deuteration of all four phenolic ortho-positions (3',3'',5',5''); 2. acid catalyzed deuteration of the olefin bridge with subsequent formation of deuterated psi-DES (3 or 4). Due to the equilibration between DES, psi-DES, and Z-diethylstilbestrol (cis-DES) in the acidic reaction mixture at 85 degrees C, the deuterated psi-DES is thought to rapidly rearrange to deuterated DES. Repeated deuteration will eventually form DES-d8 fully labeled in the 2,2,5,5 methylene positions.
Steroids 1982 Dec
PMID:Deuterium labeling of diethylstilbestrol and analogues. 718 18

This study reports the formation and isolation of a diethylstibestrol-dimethylsulfoxide (DES-DMSO) adjunct and Z-3, 4-di (p-hydroxyphenyl)-2-hexene (psi-DES) from trans-DES. The presence of psi-DES was indicated by NMR and mass spectrometry and confirmed by direct comparison to a reference sample. High resolution NMR (360 MHz) along with the comparison of the chemical shift values of methine and methyl protons attached to carbon-carbon double bonds in Z and E isomers of 3-substituted-2-pentenes and dienestrol derivatives were used in postulating the Z-stereochemistry for psi-DES. A NMR additive increment method was useful for the comparison of the chemical shift values of methine protons in psi-DES and other literature compounds. Nuclear Overhauser Enhancement (NOE) confirmed the Z-stereochemistry of psi-DES.
Steroids 1981 Nov
PMID:Isomerization of trans-diethylstilbestrol to pseudo-diethylstilbestrol. 732 87