Development of increased cytoplasmic binding of androgen in the submandibular gland of the mouse with testicular feminization

A new catabolite with a 2 carbon shorter side chain and a trans ureido ring, d allobisnorbiotin, was isolated from the culture filtrates of a pseudomonad grown on double labeled d biotin. Most of the original ureido carbonyl ¹⁴C of biotin was lost but ³H in the thiolane ring and the side chain portion is retained in the catabolite. Maximal amounts of d allobisnorbiotin are formed under conditions for bacterial growth where aeration is limited. Formation of this catabolite must occur from the level of bisnorbiotin by way of cleavage of the cis ureido ring at the bridgehead carbon opposite the side chain, followed by decarbamylation and recarbamylation to form the trans isomer.