Synthesis of N-acetylxylosamidoxime, a potential transition state analog inhibitor of glycosyltransferases

The synthesis of a polyfunctionalized amidoxime is described involving condensation of hydroxylamine on a thioamide deriving from Boc-l-serine. This structure could be an efficient transition state like inhibitor of N-acetylglucosaminyltransferases, such as chitin synthase.