Stereochemistry associated with the conversion of C-3 of serine through methylenetetrahydrofolate and methenyltetrahydrofolate in the biosynthesis of tuberin.

KM Cable, RB Herbert, V Bertram, DW Young

Index: Cable; Herbert; Bertram; Young Tetrahedron Letters, 1987 , vol. 28, # 35 p. 4101 - 4104

Full Text: HTML

Citation Number: 8

Abstract

Summary: Results of feeding experiments in Streptomyces amakusaensis with (22, 3R)-[3- 2H,]-and (22, 3g)-[2, 3-2H2]-serine show that the F-formyl group in tuberin (1) is formed from C-3 of serine via tetrahydrofolate-linked intermediates with retention of the 3-pro-S--proton; retention is only partially stereospecific. The relevance to tetrahydrololate metabolism is discussed.