Enzymatic glycosylation using 6-O-acylated sugar donors and acceptors: β-N-acetylhexosaminidase-catalysed synthesis of 6-O,N,N′-triacetylchitobiose and 6′-O,N,N′-triacetylchitobiose

Abstract p -Nitrophenyl 6- O -acetyl-2-acetamido-2-deoxy-β- d -glucopyranoside ( 5a ) was used as the glycosyl donor in a β- N -acetylhexosaminidase-catalysed (from Penicillium brasilianum ) glycosylation of GlcNAc yielding 6′- O , N , N ′-triacetylchitobiose ( 6 ), while 6- O -acetyl-2-acetamido-2-deoxy-β- d -glucopyranose ( 3a ) served as a selectively protected acceptor in a transglycosylation reaction catalysed by the same enzyme to yield 6- O , N , N ′-triacetylchitobiose ( 4 ).