Studies on the non-mevalonate isoprenoid biosynthetic pathway. Simple methods for preparation of isotope-labeled (E)-1-hydroxy-2-methylbut-2-enyl 4-diphosphate

Abstract

(E)-1-Hydroxy-2-methylbut-2-enyl 4-diphosphate (6) has been recently detected as an intermediate of isoprenoid biosynthesis via 1-deoxy-D-xylulose 5-phosphate. The compound was synthesized in two steps from 2-methyl-2-vinyloxirane with an overall yield of 72%. We also report a method affording [1-H-3]-6 and [1-H-2(1)]-6 from the same starting material in four steps where the hydrogen isotope is introduced in the last reaction step from deuterated or tritiated sodium borohydride. The radiochemical yield of [1-H-3]-6 was 15%. (C) 2002 Elsevier Science Ltd. All rights reserved.