The synthesis of four bifunctionalized orthogonally N-protected oligosaccharides derived from lactose and mannose, intended as cross-linking derivatives, is described. The amino sugar at the non-reducing end is derivatized with an N-Boc-protected glycine moiety, and further connected
IntroductionTo study biological processes, appropriate cross-linking molecules are often required to circumvent the synthesis of complex oligosaccharides. A challenge within the field of glycobiology and biotechnology is to achieve controlled immobilization of proteins onto surfaces, 2 while retaining their biological features and properties.
Results and discussionThe azido sugar 6 was synthesized starting from the known thioglycoside 5 30 using triflic anhydride followed by NaN 3 displacement, giving the azido functionalized derivative 6 as a crystalline compound in 85% yield (Scheme 1).