Enzymatic glycosylation using 6-O-acylated sugar donors and acceptors: beta-N-acetylhexosaminidase-catalysed synthesis of 6-O,N,N'-triacetylchitobiose and 6'-O,N,N'-triacetylchitobiose.
p-Nitrophenyl 6-O-acetyl-2-acetamido-2-deoxy-beta-D-glucopyranoside (5a) was used as the glycosyl donor in a beta-N-acetylhexosaminidase-catalysed (from Penicillium brasilianum) glycosylation of GlcNAc yielding 6'-O,N,N'-triacetylchitobiose (6), while 6-O-acetyl-2-acetamido-2-deoxy-beta-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).
Husáková
L
L
Laboratory of Biotransformation, Institute of Microbiology, Academy of Sciences of the Czech Republic, Prague.
Riva
S
S
Casali
M
M
Nicotra
S
S
Kuzma
M
M
Hunková
Z
Z
Kren
V
V
D001236:Aspergillus oryzae / Q000201:enzymology; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D010407:Penicillium / Q000201:enzymology; D001619:beta-N-Acetylhexosaminidases / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*
D004187:Disaccharides; C032438:chitobiose; D001619:beta-N-Acetylhexosaminidases