Batta A K, Salen G, Tint G S, Honda A, Shefer S
Department of Medicine, University of Medicine and Dentistry of New Jersey, New Jersey Medical School, Newark, USA.
Steroids. 1997 Nov;62(11):700-2. doi: 10.1016/s0039-128x(97)00070-6.
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.
描述了[3α-³H]7-脱氢胆固醇的合成方法，即通过将7-脱氢胆固醇中的5,7-二烯系统保护为与4-苯基-1,2,4-三唑啉-3,5-二酮的狄尔斯-阿尔德加合物，然后将羟基氧化得到3-氧代加合物。用[³H]硼氢化钠还原酮加合物得到[3α-³H]7-脱氢胆固醇的加合物，通过用氢化铝锂处理从中获得放射性标记的甾醇。该方法的优点是可以制备高标记的[3α-³H]7-脱氢胆固醇。此外，与7-脱氢胆固醇不同，它与4-苯基-1,2,4-三唑啉-3,5-二酮的加合物是稳定的，可以储存。这使得能够制备小批量的[3α-³H]7-脱氢胆固醇以立即用于生物学实验，并将由于过量放射性标记的7-脱氢胆固醇分解而导致的损失降至最低。
