Steroid HormoneのRadioimmunoassayにおける抗原の立体構造と抗体の特異性との相関(第2報)6-Hydroxytestosterone 6-Hemisuccinate-Bovine Serum Albumin Conjugateの合成

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3,3-Ethylenedioxy-5α, 6α-epoxyandrostan-17β-ol (I), derived from testosterone, was oxidized with glacial acetic acid and then hydrolyzed with 80% acetic acid to give 6β-hydroxytestosterone 6-acetate (IIb). The conversion of IIb to 6α-hydroxytestosterone 6-acetate (IIa) was achieved by treatment with HCl gas in CHCl_3 containing EtOH (0.7%). The trityl derivatives of IIa and IIb were hydrolyzed with K_2CO_3 to produce 6α (or 6β)-hydroxy-17β-trityloxy-4-androsten-3-one (IVa, IVb), respectively. The succinylation of IVa and IVb with succinic anhydride followed by hydrolysis with 50% acetic acid afforded 6α (or 6β)-hydroxytestosterone 6-hemisuccinate (VIa, VIb), respectively. VIa and VIb were attached to bovine serum albumin via mixed anhydride coupling using tributy1amine and isobutyl chloroformate.
1976-02-25