Title | Efficient chemoenzymatic synthesis of ADP-D-glycero-beta-D-manno-heptose and a mechanistic study of ADP-L-glycero-D-manno-heptose 6-epimerase |
Publication Type | Journal Article |
Year of Publication | 2005 |
Authors | Read, JA, Ahmed, RA, Tanner, ME |
Journal | Organic Letters |
Volume | 7 |
Pagination | 2457-2460 |
Date Published | Jun |
Type of Article | Article |
ISBN Number | 1523-7060 |
Keywords | biosynthesis, 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 |
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