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

✍ Scribed by Stefan Hecht; Sabine Amslinger; Johann Jauch; Klaus Kis; Viola Trentinaglia; Petra Adam; Wolfgang Eisenreich; Adelbert Bacher; Felix Rohdich


Book ID
104252362
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
96 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis


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 [1-3 H]-6 and [1-2 H 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 [1-3 H]-6 was 15%.