Transfer RNA components. Part II. Reactions of heavy metal salts of 2-thiouracil and a synthesis of 2-thiouridine

Abstract

The condensation of various heavy metal salts of 2-thiouracil with glycosyl halides has been investigated. Both the chloromercury and bromomercury salts of 2-thiouracil give N(1)-glycosides exclusively, and the use of the bromomercury salt in a synthesis of 2-thiouridine is described. Reactions of the chloromercury, silver, and thallium salts of 2-thiouracil with acetobromoglucose can also give an S(2),O(4)-diglucoside and an S(2)-monoglucoside. The mechanisms of the formation of these glycosides and their rearrangement of the N(1)-glucosides are discussed.