Thermal decomposition of beta-D-galactopyranosyl-(1-->3)-2-acetamido-2-deoxy-D-hexopyranoses under neutral conditions

Carbohydrate Research
Kazuhiro ChikuMotomitsu Kitaoka

Abstract

beta-d-Galactopyranosyl-(1-->3)-2-acetamido-2-deoxy-d-glucose (LNB) and beta-d-galactopyranosyl-(1-->3)-2-acetamido-2-deoxy-d-galactose (GNB) decompose rapidly upon heating into d-galactose and mono-dehydrated derivatives of the corresponding 2-acetamido-2-deoxy-d-hexoses, including 2-acetamido-2,3-dideoxy-hex-2-enofuranoses and bicyclic 2-acetamido-3,6-anhydro-2-deoxy-hexofuranoses. The decomposition is conducted under neutral conditions where glycosyl linkages are generally believed to be stable. The half-lives of LNB and GNB were 8.1min and 20min, respectively, at 90 degrees C and pH 7.5. The pH dependency of decomposition rates suggests that the instabilities are an extension of the conditions for the peeling reaction, often observed with glycans of O-linked glycoproteins under alkaline conditions. Such decomposition under the neutral conditions is commonly observed with 3-O-linked reducing aldoses.

References

Feb 1, 1977·Carbohydrate Research·J M BeauP Sinaÿ
Dec 1, 1968·Proceedings of the National Academy of Sciences of the United States of America·K O Lloyd, E A Kabat
Jun 15, 1984·Science·G F Springer
Aug 1, 1993·Archives of Biochemistry and Biophysics·M KitaokaH Taniguchi
Nov 26, 1999·Biochimica Et Biophysica Acta·E G Berger
Apr 20, 2001·Biological Chemistry·F G Hanisch
Apr 2, 2002·Glycoconjugate Journal·T UrashimaM Messer
Jul 16, 1963·Biochimica Et Biophysica Acta·B ANDERSONK MEYER
Jun 4, 2005·Applied and Environmental Microbiology·Motomitsu KitaokaMamoru Nishimoto
Aug 11, 2007·Bioscience, Biotechnology, and Biochemistry·Mamoru Nishimoto, Motomitsu Kitaoka
Aug 22, 2007·Analytical Biochemistry·Takanori NihiraMotomitsu Kitaoka

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Citations

Dec 15, 2010·Bioscience, Biotechnology, and Biochemistry·Shinya Fushinobu
Dec 13, 2016·Inorganic Chemistry·Xiu-Ying ZhengLan-Sun Zheng
Jan 20, 2019·Journal of Applied Glycoscience·Kazuhiro ChikuMotomitsu Kitaoka

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