PMID: 8595258Oct 1, 1995Paper

Enzymic synthesis of lacto-N-triose II and its positional analogues

Glycoconjugate Journal
Y MatahiraT Usui

Abstract

N-acetylhexosaminidase from Nocardia orientalis catalysed the synthesis of lacto-N-triose II glycoside (beta-D-GlcNAc-(1-3)-beta-D-Gal-(1-4)-beta-D-Glc-OMe, 3) with its isomers beta-D-GlcNAc-(1-6)-beta-D-Gal-(1-4)-beta-d-Glc-OMe (4) and beta-D-Gal-(1-4)-[beta-D-GlcNAc-(1-6)]-beta-D-Glc-OMe (5) through N-acetylglucosaminyl transfer from N,N'-diacetylchitobiose (GlcNAc2) to methyl beta-lactoside. The enzyme formed the mixture of trisaccharides 3, 4 and 5 in 17% overall yield based on GlcNAc2, in a ratio of 20:21:59. With p-nitrophenyl beta-lactoside as an acceptor, the enzyme also produced p-nitrophenyl beta-lacto-N-trioside II (beta-D-GlcNAc-(1-3)-beta-D-Gal-(1-4)-beta-D-Glc-OC6H4NO2-p, 6) with its isomers beta-D-GlcNAc-(1-6)-beta-D-Gal-(1-4)-beta-D-Glc-OC6H4NO2-p (7) and beta-D-Gal-(1-4)-[beta-D-GlcNAc-(1-6)]-beta-D-Glc-OC6H4NO2-p (8). In this case, when an inclusion complex of p-nitrophenyl lactoside acceptor with beta-cyclodextrin was used the regioselectivity of glycosidase-catalysed formation of trisaccharide glycoside was substantially changed. It resulted not only in a significant increase of the overall yield of transfer products, but also in the proportion of the desired compound 6.

References

May 15, 1979·European Journal of Biochemistry·J KościelakW Dzierzkowa-Borodej
Aug 1, 1990·Agricultural and Biological Chemistry·A KondoT Ikenaka
Sep 5, 1990·Carbohydrate Research·K G Nilsson
Jan 1, 1981·Annual Review of Biochemistry·S Hakomori

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Citations

Apr 7, 2015·Applied Microbiology and Biotechnology·Christian NyffeneggerJørn Dalgaard Mikkelsen
Jun 19, 2018·Chembiochem : a European Journal of Chemical Biology·Shariza B JamekAnne S Meyer
Jan 24, 2016·New Biotechnology·Birgitte ZeunerAnne S Meyer
May 5, 2010·Biotechnology Advances·Kristýna SlámováVladimír Kren

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