Synthesis of TDP-3-amino-3,4,6-trideoxy-alpha-D-xylo-hexopyranose--the immediate precursor of TDP-alpha-D-desosamine.
A synthetic pathway producing the title compound starting from methyl alpha-D-glucose is described. This compound was shown to be a substrate for DesVI, an AdoMet-dependent methyltransferase which catalyzes N,N-dimethylation of the title compound to give a biological significant unusual sugar, desosamine.
Chang
Cheng-Wei T
CW
Division of Medicinal Chemistry, College of Pharmacy, University of Texas, Austin 78712, USA.
Liu
Hung-wen
HW
D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D000900:Anti-Bacterial Agents / Q000096:biosynthesis; D006868:Hydrolysis / Q000187:drug effects; D008049:Lipase / Q000737:chemistry / Q000378:metabolism; D018942:Macrolides; D013237:Stereoisomerism; D013306:Streptomycetaceae / Q000378:metabolism
D000606:Amino Sugars; D000900:Anti-Bacterial Agents; D018942:Macrolides; C467609:TDP-3-amino-3,4,6-trideoxy-xylo-hexopyranose; C008517:methymycin; C110125:desosamine; D008049:Lipase