Study of the (1,7)-sigmatropic shift of a 1-hydroxylated 3-desoxy previtamin D to vitamin D: observation of a modest primary deuterium kinetic isotope effect/sup 1/
Studies of 19,19,19-trideuteriated derivatives of previtamin D/sub 3/ and their various 1-hydroxylated counterparts invite the possibility of utilizing previtamins as biochemical or chemical research tools. It is anticipated that a heavy isotope at C-19 will attenuate the rate of the (1,7)-sigmatropic shift so as to facilitate handling of the thermally unstable previtamins. Thus, in the case of 1..cap alpha..,25-dihydroxyvitamin D/sub 3/, its previtamin form might be anticipated to exist in nature, and its more stable 19,19,19-trideuterio counterpart would facilitate evaluation of its biological profile. Moreover, the latter might have practical application as a slow release source of the highly potent, and potentially toxic, natural hormone. In this communication the authors describe their initial studies in this area through kinetic investigations of the isomerization of 3-deoxy-1-hydroxyprevitamin D/sub 3/ epimers, a (1,7)-sigmatropic shift model for the previtamin form of the natural hormone.
- Research Organization:
- Univ. of California, Riverside (USA)
- OSTI ID:
- 5353213
- Journal Information:
- J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 110:3; ISSN JACSA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400202* -- Isotope Effects
Isotope Exchange
& Isotope Separation
ALKALI METAL COMPOUNDS
BROMIDES
BROMINE COMPOUNDS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
DATA
DEUTERIUM
DEUTERIUM COMPOUNDS
EXPERIMENTAL DATA
FURANS
HALIDES
HALOGEN COMPOUNDS
HETEROCYCLIC COMPOUNDS
HYDROGEN COMPOUNDS
HYDROGEN ISOTOPES
INFORMATION
ISOTOPE EFFECTS
ISOTOPES
KINETICS
LIGHT NUCLEI
LITHIUM BROMIDES
LITHIUM COMPOUNDS
LITHIUM HALIDES
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
REACTION KINETICS
STABLE ISOTOPES
TETRAHYDROFURAN
VITAMIN D
VITAMINS