Comparison of chemical and enzymatic synthesis of 2-acetamido-2-deoxy-D-mannose 6-phosphate: a new approach.
Chemical and enzymatic methods to synthesis of 2-acetamido-2-deoxy-D-mannose-6-phosphate (ManNAc-6-P) have been investigated. A new preparative method has been developed although some established procedures were tried. In this new method, a 6-O-acetyl or 4,6-di-O-acetyl group of the per-O-acetylated 2-acetamido-2-deoxy-D-mannose (ManNAc) were regioselectively removed with an esterase from the yellow yeast, Rhodosporidium toruloides, followed by phosphorylation and O-deacetylation under mild conditions. 1H and 13C NMR data spectra of ManNAc-6-P were recorded.
Department of Biology, Johns Hopkins University, Baltimore, MD 21218, USA.
M Z
MZ
Liu
Y C
YC
Lee
D000107:Acetylation; D001487:Basidiomycota / Q000201:enzymology; D002236:Carbohydrate Conformation; D004950:Esterases / Q000378:metabolism; D006595:Hexosamines / Q000737:chemistry* / Q000378:metabolism*; D007202:Indicators and Reagents; D008360:Mannosephosphates / Q000138:chemical synthesis* / Q000378:metabolism; D008958:Models, Molecular; D010766:Phosphorylation
C430285:2-acetamido-2-deoxy-mannose-6-phosphate; D006595:Hexosamines; D007202:Indicators and Reagents; D008360:Mannosephosphates; D004950:Esterases; C002022:N-acetylmannosamine