NDLI: Synthesis of [3α-3H]7-dehydrocholesterol via stable tritiated 4-phenyl-1,2,4-triazoline-3,5-dione derivative

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Synthesis of [3α-3H]7-dehydrocholesterol via stable tritiated 4-phenyl-1,2,4-triazoline-3,5-dione derivative

Content Provider	Semantic Scholar
Author	Batta, Ashok Kumar Salen, Gerald Tint, G. Stephen Honda, Akira Shefer, Sarah
Copyright Year	1997
Abstract	Synthesis of [3 alpha-3H]7-dehydrocholesterol is described via protection of the 5,7-diene system in 7-dehydrocholesterol as the Diels-Alder adduct with 4-phenyl-1,2,4-triazoline-3,5-dione followed by oxidation of the hydroxyl group to give the 3-oxo adduct. Reduction of the keto adduct with [3H]sodium borohydride produced the adduct of [3 alpha-3H]7-dehydrocholesterol from which the radiolabeled sterol was obtained via treatment with lithium aluminum hydride. The advantage of the method is that highly labeled [3 alpha-3H]7-dehydrocholesterol can be prepared. Further, unlike 7-dehydrocholesterol, its adduct with 4-phenyl-1,2,4-triazoline-3,5-dione is stable and can be stored. This allows the preparation of small batches of [3 alpha-3H]7-dehydrocholesterol for immediate use in biological experiments, and losses due to decomposition of excess radiolabeled 7-dehydrocholesterol are minimized.
Starting Page	700
Ending Page	702
Page Count	3
File Format	PDF HTM / HTML
DOI	10.1016/S0039-128X(97)00070-6
Alternate Webpage(s)	https://api.elsevier.com/content/article/pii/S0039128X97000706
Alternate Webpage(s)	https://www.sciencedirect.com/science/article/pii/S0039128X97000706?dgcid=api_sd_search-api-endpoint
PubMed reference number	9366008
Alternate Webpage(s)	https://doi.org/10.1016/S0039-128X%2897%2900070-6
Journal	Medline
Volume Number	62
Journal	Steroids
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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