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.