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On the effect of the aglycon structure of three aryl beta-D-galactosides on the yield and the regioselecttvity of the transglycolytic synthesis of N-acetyllactosamine
We examined the effect as donors of three aryl beta-D-galactosides (i.e. p-nitrophenyl beta-D-galactopyranoside, o-nitrophenyl beta-D-galactopyranoside and phenyl beta-D-galactopyranoside) on the regioselectivity and the yield of the synthesis of N-acetyllactosamine obtained from the transglycosylation reaction catalyzed by a crude preparation of beta-D-galactosidase from Bacillus circulans at 25C, 37C and 55C, respectively. Using p-nitrophenyl beta-D-galactopyranoside the reaction results were fully regiospecific at all the temperatures considered: the maximum molar yield (74%) was obtained at an incubation temperature of 55C Using o-nitrophenyl beta-D-galactopyranoside as the donor the reaction was still highly regioselective and the maximum molar yield (50%) was achieved at an incubation temperature also of 55C. Using phenyl beta-D-galactopyranoside transglycolytic products appear only at an incubation temperature of 55C but at very low molar yield (about 14%) and lower regioselectivity.
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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics