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Efficient chemoenzymatic synthesis of ADP-D-glycero-beta-D-manno-heptose and a mechanistic study of ADP-L-glycero-D-manno-heptose 6-epimerase

TitleEfficient chemoenzymatic synthesis of ADP-D-glycero-beta-D-manno-heptose and a mechanistic study of ADP-L-glycero-D-manno-heptose 6-epimerase
Publication TypeJournal Article
Year of Publication2005
AuthorsRead, JA, Ahmed, RA, Tanner, ME
JournalOrganic Letters
Volume7
Pagination2457-2460
Date PublishedJun
Type of ArticleArticle
ISBN Number1523-7060
Keywordsbiosynthesis, CARBON, D-MANNOHEPTOSE 6-EPIMERASE, EPIMERIZATION, PATHWAY
Abstract

[GRAPHICS] A chemoenzymatic synthesis of ADP-D-glycero-β-D-manno-heptose (ADP-D,D-Hep) is described in which D,D-Hep 7-phosphate is converted to ADP-D,D-Hep by two biosynthetic enzymes. This strategy allows access to the 6"-deuterated analogue, which upon incubation with the epimerase showed complete retention of the isotopic label at the 6"-position. This provides evidence for a direct oxidation mechanism in which the hydride initially transferred to the NADP(+) cofactor is subsequently returned to the same carbon in a nonstereospecific manner.

URL<Go to ISI>://000229574300042