Synthesis of enantiopure 2-C-methyl-D-erythritol 4-phosphate and 2,4-cyclodiphosphate from D-arabitol.
[reaction: see text] Two key intermediates of the newly discovered mevalonate-independent pathway for isoprenoid biosynthesis were prepared. Optically pure 2-C-methyl-D-erythritol 4-phosphate and 2,4-cyclodiphosphate were chemically synthesized from D-arabitol using a convenient benzylidene and tert-butyldimethylsilyl protection of polyhydroxylated intermediates. The new scheme offers a straightforward route to analogues and labeled forms.
Urbansky
Marek
M
Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, USA.
Davis
Chad E
CE
Surjan
Jacob D
JD
Coates
Robert M
RM
D004896:Erythritol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D008956:Models, Chemical; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D013403:Sugar Phosphates / Q000138:chemical synthesis*
C114232:2-C-methylerythritol 4-phosphate; D013402:Sugar Alcohols; D013403:Sugar Phosphates; C443879:methyl-D-erythritol 2,4-cyclodiphosphate; D004896:Erythritol; C014999:arabitol