PMID: 2510824Sep 5, 1989Paper

Transfer of synthetic sialic acid analogues to N- and O-linked glycoprotein glycans using four different mammalian sialyltransferases

Biochemistry
H J GrossR Brossmer

Abstract

This paper presents kinetic properties of the transfer of several synthetic 9-substituted sialic acid analogues onto N- or O-linked glycoprotein glycans by four purified mammalian sialyltransferases: Gal beta 1,4GlcNac alpha 2,6sialyltransferase, Gal beta-1,4(3)GlcNAc alpha 2,3-sialyltransferase, Gal beta 1,3GalNAc alpha 2,3sialyltransferase, and GalNAc alpha 2,6sialyltransferase. The substituents at C-9 of the sialic acid analogues introduce special biochemical characteristics: 9-Amino-NeuAc represents, up to the present, the first derivative that is resistant toward bacterial, viral, and mammalian sialidases but is transferred by a sialyltransferase. 9-Acetamido-NeuAc, 9-benzamido-NeuAc, and 9-hexanoylamido-NeuAc differ in size and hydrophobic character from each other and from parent NeuAc. 9-Azido-NeuAc may be used to introduce a photoreactive label. The kinetic properties of the four sialyltransferases with regard to the donor CMP-glycosides differed distinctly depending on the structure of the substituent at C-9. CMP-9-amino-NeuAc was only accepted as donor substrate by Gal beta 1,4GlcNAc alpha 2,6sialyltransferase (rat liver), but the Km value was 14-fold higher than that of parent CMP-NeuAc. In contrast, 9-azido-NeuAc w...Continue Reading

References

Nov 15, 1988·European Journal of Biochemistry·H J Gross, R Brossmer
Jan 1, 1986·Annual Review of Biophysics and Biophysical Chemistry·R E FeeneyY Yeh
Nov 2, 1987·European Journal of Biochemistry·H J GrossR Brossmer
May 1, 1980·European Journal of Biochemistry·J M Beau, R Schauer
Oct 1, 1980·Proceedings of the National Academy of Sciences of the United States of America·M A Markwell, J C Paulson

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Citations

Apr 12, 2002·Chembiochem : a European Journal of Chemical Biology·T BülterL Elling
Feb 1, 1991·Glycoconjugate Journal·U SticherR Brossmer
Nov 28, 1997·Applied Biochemistry and Biotechnology·Z Guo, P G Wang
Nov 1, 2011·Annals of Biomedical Engineering·Ruben T AlmarazKevin J Yarema
Aug 14, 2009·Glycobiology·Jian DuKevin J Yarema
Nov 18, 2010·Glycobiology·Zhengliang L WuWeiping Jiang
Apr 23, 2004·Biological Chemistry·Yanqin ShenRoland Schauer
Jan 10, 1994·FEBS Letters·U SchwarzR Brossmer
Feb 27, 2003·European Journal of Biochemistry·Marie-Ange Krzewinski-RecchiPhilippe Delannoy
May 30, 2008·Carbohydrate Research·Jana RauvolfovaGeert-Jan Boons
May 11, 2015·Glycoconjugate Journal·Nam D PhamJennifer J Kohler
Jul 31, 2007·Biochemical and Biophysical Research Communications·Yanhong LiXi Chen
May 1, 1992·Analytical Biochemistry·Y IchikawaC H Wong
Jan 27, 2012·ACS Chemical Biology·Sabrina PouillyVéronique Piller
May 24, 2006·Glycobiology·Shawn DeFreesHenrik Clausen
Dec 26, 2001·The Journal of Biological Chemistry·Cornelia OetkeMichael Pawlita
Nov 30, 2019·Nature Reviews. Chemistry·Christian AgatemorKevin J Yarema
Jan 27, 1995·The Journal of Biological Chemistry·A K Datta, J C Paulson
Jun 9, 2001·The Journal of Organic Chemistry·W NotzR R Schmidt

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