Chemo-enzymic synthesis of guanosine 5′-diphosphomannose (GDP-mannose) and selected analogues

Abstract

Guanosine 5′-diphosphomannose (GDP-mannose, 1) has been prepared via two routes from α-D-mannose 1-phosphate 5. The non-enzymic route involves coupling of the phosphate 5 to guanosine 5′-monophosphate dibutyl phosphinothioc anhydride (GMP-anhydride 11) to give compound 1 in 40% yield. The enzymic routes require coupling of compound 5 with guanosine 5′-triphosphate (GTP) catalysed by GDP-mannose pyrophosphorylase (37% yield).