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 Original Research Article

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).