High performance polymer supports for enzyme-assisted synthesis of glycoconjugates

Carbohydrate Research
K YamadaS Nishimura

Abstract

Efficient and practical methodology for the construction of carbohydrates, including oligosaccharide derivatives and sphingoglycolipids, was established on the basis of a water-soluble polymer supports having unique linkers that can be cleaved by specific conditions. Novel glycomonomers for the construction of polymer supports were synthesized and copolymerized with acrylamide to give three types of water-soluble glycopolymers having primer sugars through the specific linkers containing (i) p-substituted benzyl group, (ii) L-phenylalanine residue, and (iii) ceramide-mimetic L-serine derivative, respectively. These glycopolymers were employed for sugar elongation reactions with glycosyl transferases such as GlcNAc beta 1,4-galactosyl transferase, beta Gall-->3/4GlcNAc alpha-2,6-sialyl transferase, and beta Gall-->3/4GlcNAc alpha-2,3-sialyl transferase in the presence of each sugar nucleotide as glycosyl donor to afford polymers having N-acetyllactosamine, sialyl alpha-(2-->6) N-acetyllactosamine, and sialyl alpha-(2-->3) lactose residues in excellent yield. Subsequent hydrogenolysis, hydrolysis with alpha-chymotrypsin, or transglycosylation to ceramide with ceramide glycanase proceeds smoothly to give N-acetyllactosamine, a vers...Continue Reading

References

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Citations

Nov 28, 2000·Carbohydrate Research·R I Duclos
Dec 22, 1999·Current Opinion in Biotechnology·M M Palcic
Apr 21, 1999·Current Opinion in Biotechnology·D H Altreuter, D S Clark
Jan 16, 2002·Drug Discovery Today·Reinhard ReentsHerbert Waldmann
Aug 2, 2001·Current Opinion in Chemical Biology·S Nishimura
Jun 1, 2002·Current Opinion in Chemical Biology·Joseph O RichYuri L Khmelnitsky
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Dec 1, 2011·Angewandte Chemie·Che-Hsiung HsuChi-Huey Wong
Feb 13, 2013·Chemistry : a European Journal·Juan EtxebarriaNiels-Christian Reichardt
Jun 15, 2006·Chemistry : a European Journal·Noriko Nagahori, Shin-Ichiro Nishimura
Oct 28, 2019·International Journal of Molecular Sciences·Luuk MestromPeter-Leon Hagedoorn
Feb 24, 2007·Glycobiology·Satoshi UemuraJin-Ichi Inokuchi
Jun 8, 2021·Angewandte Chemie·Skander A AbboudVincent Aucagne
Nov 3, 2010·Journal of the American Chemical Society·Takahiko MatsushitaShin-Ichiro Nishimura
Jul 17, 2018·Chemical Reviews·Liuqing WenPeng George Wang
Oct 3, 2008·Carbohydrate Research·Yoshimi HagaKenichi Hatanaka
May 22, 2010·Bioorganic & Medicinal Chemistry Letters·Fei FengShin-Ichiro Nishimura
Jul 14, 2010·Bioorganic & Medicinal Chemistry Letters·Koji MatsuokaDaiyo Terunuma

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