Synthesis of neoglycoconjugates by transglycosylation with Arthrobacter protophormiae endo-beta-N-acetylglucosaminidase. Demonstration of a macro-cluster effect for mannose-binding proteins.

The Journal of Biological Chemistry
J Q FanY C Lee

Abstract

The transglycosylation activity of endo-beta-N-acetylglucosaminidase from Arthrobacter protophormiae (endo-A) can be enhanced dramatically by inclusion of organic solvent in the reaction mixture (see accompanying article; Fan, J.-Q., Takegawa, K., Iwahara, S., Kondo, A., Kato, I., Abeygunawardana, C., and Lee, Y. C. (1995) J. Biol. Chem. 270, 17723-17729). This finding was extended to synthesis of important intermediates for preparation of neoglycoconjugates. When 0.2 M GlcNAc-O-(CH2)6NH2, GlcNAc-O-CH2CH = CH2, GlcNAc-O-(CH2)3-CH = CH2, GlcNAc-O-(CH2)3NHCOCH = CH2, GlcNAc-S-CH2CN, GlcNAc-S-(CH2)3CH3, or GlcNAc-S-CH2-CONHCH2CH(OMe)2 were used as acceptors in 30% acetone-containing media, the transglycosylation was accomplished with about 80% yield. The transglycosylation yields to benzyl beta-GlcNAc (67%), 4-methyl-umbelliferyl beta-GlcNAc (66%), p-nitrophenyl beta-GlcNAc (33%), and (GlcNAc-beta-S-CH2CH2CH2)2 (43%) were lower, because their poor solubilities allowed only 0.05 M or lower concentrations in the reaction mixture. A micromole-scale synthesis of Man9GlcNAc2-O-(CH2)3-NHCOCH = CH2 (Man9GlcNAc2-NAP) was accomplished with 90% yield, and the structure of the transglycosylation product was confirmed by 1H NMR. Man9GlcNAc2-N...Continue Reading

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Citations

Dec 28, 1999·Analytical Biochemistry·N Yoshitani, S Takasaki
Jun 13, 2001·Biochemical and Biophysical Research Communications·K Fujita, K Takegawa
May 9, 2001·Biochemical and Biophysical Research Communications·K Fujita, K Takegawa
Jul 1, 1996·Journal of Biomedical Science·Y.C. Lee, R.T. Lee
Oct 1, 1996·Current Opinion in Structural Biology·R Roy
Nov 5, 1997·Current Opinion in Structural Biology·G M WattS L Flitsch
Jun 1, 2004·Bioscience, Biotechnology, and Biochemistry·K FujitaKaoru Takegawa
Feb 8, 2005·Biochemical and Biophysical Research Communications·Steven HauserLai-Xi Wang
Jun 3, 2004·Chembiochem : a European Journal of Chemical Biology·Maja KöhnJosé M García Fernández
Mar 15, 2016·Angewandte Chemie·Pragya PriyankaAntony J Fairbanks
Jan 1, 2011·Trends in Glycoscience and Glycotechnology : TIGG·Lai-Xi Wang

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