On the effect of the aglycon structure of three aryl β-D-galactosides on the yield and the regioselecttvity of the transglycolytic synthesis of N-acetyllactosamine

Article abstract of DOI:10.1080/07328309908544015

We examined the effect as donors of three aryl β-D-galactosides (i.e. p-nitrophenyl β-D-galactopyranoside, o-nitrophenyl β-D-galactopyranoside and phenyl β-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 β-D-galactosidase from Bacillus circulans at 25°C, 37°C and 55°C, respectively. Using p-nitrophenyl β-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 55°C Using o-nitrophenyl β-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 55°C. Using phenyl β-D-galactopyranoside transglycolytic products appear only at an incubation temperature of 55°C but at very low molar yield (about 14%) and lower regioselectivity.

Full text of DOI:10.1080/07328309908544015

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Journal of Carbohydrate Chemistry
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On the Effect of the Aglycon
Structure of Three Aryl β-D-
Galactosides on the Yield and
the Regioselectivity of the
Transglycolytic Synthesis of N-
Acetyllactosamine
Amedeo Vetere , Lara Novelli & Sergio Paoletti
a Department of Biochemistry, Biophysics and
Macromolecular Chemistry , University of Trieste , Via L.
Giorgieri 1, I-34127 Trieste, Italy
b Department of Biochemistry, Biophysics and
Macromolecular Chemistry , University of Trieste , Via L.
Giorgieri 1, I-34127 Trieste, Italy
c Department of Biochemistry, Biophysics and
Macromolecular Chemistry , University of Trieste , Via L.
Giorgieri 1, I-34127 Trieste, Italy
Published online: 27 Feb 2008.
To cite this article: Amedeo Vetere , Lara Novelli & Sergio Paoletti (1999) On the Effect of the
Aglycon Structure of Three Aryl β-D-Galactosides on the Yield and the Regioselectivity of the
Transglycolytic Synthesis of N-Acetyllactosamine, Journal of Carbohydrate Chemistry, 18:5,
515-521, DOI: 10.1080/07328309908544015
To link to this article: http://dx.doi.org/10.1080/07328309908544015
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