Regioselective synthesis of p-nitrophenyl glycosides of β-d-galactopyranosyl-disaccharides by transglycosylation with β-d-galactosidases

An original chemoenzymatic route for the synthesis of β-d-galactofuranosides using an α-l-arabinofuranosidase

“…35 Likewise, taken together, our findings infer that in hydrolytic mode AbfD3 should preferentially cleave (1!2) linkages. In our previous study, based on the findings of others, [36][37][38] we suggested that the high regioselectivity of reactions involving PhCH 2 -Xylp might be correlated to the a configuration of the anomeric carbon in this sugar derivative. These present data add further weight to this argument, but do not provide confirmation because the equivalent b anomer was not tested.…”

Synthesis of pentose-containing disaccharides using a thermostable α-l-arabinofuranosidase

“…Moreover, numerous investigations have shown that reaction conditions, the nature and the anomeric configuration of the aglycon moiety of the acceptor 8;22;23 and the exact source of the enzymes influence regioselectivity. [23][24][25] Importantly, it is also known that frequently the regioselectivity of the transglycosylation reaction can be directly correlated to the hydrolytic specificity of glycoside hydrolases. 6 In the case of AbfD3, it has been previously shown that this enzyme can hydrolyse both the a-(1 fi 2) and a-(1 fi 3) bonds in arabinoxylans and, to a lesser extent, the a-(1 fi 5) bond in arabinan.…”

Enzyme-catalysed synthesis of galactosylated 1d- and 1l-chiro-inositol, 1d-pinitol, myo-inositol and selected derivatives using the β-galactosidase from the thermophile Thermoanaerobacter sp. strain TP6-B1

“…12;16-18 Recently, considerable interest has focussed on the use of glycoside hydrolase enzymes (glycosidases) to synthesise di-and oligo-saccharides in only one step. [19][20][21][22][23][24] The particular characteristics of the glycosidase employed determines, which transglycosylation products, if any, are formed and the products formed are a function of the enzyme's acceptor and donor preferences as well as its glycosylation regio-and stereoselectivity. However, these selectivities need not be regarded as limitations to the use of glycosidases in oligosaccharide synthesis.…”