Carbohydrates are increasingly appreciated for their critical roles in
biological functions. Driving these studies addressing the molecular
basis of carbohydrate-mediated events is the availability of natural a
nd unnatural carbohydrates. Recently, new methods of enzymatic synthes
is have been developed that now afford rapid access to complex, struct
urally diverse oligosaccharides on large scales, This methodology has
been essential to gaining insight into the molecular details of import
ant carbohydrate recognition phenomena that are associated with many s
ignaling processes, This review summarizes recent chemical studies exa
mining selectin/sialyl Lewis(x) binding, a key event in inflammation a
nd metastasis, and describes the development of carbohydrate mimetics
that may offer leads to new therapeutic agents. In addition, combinato
rial synthesis has been used to prepare carbohydrate mimetics to neomy
cin B, an aminoglycoside that binds RNA involved in HIV infection, and
chemoenzymatic methodology has been applied to the design and synthes
is of mechanism-based inhibitors of glycoprocessing enzymes.