Literature DB >> 10211700

Synthesis of Gal-beta-(1-->4)-GlcNac-beta-(1-->6)-[Gal-beta-(1-->3]-GalNAc-alpha- OBn oligosaccharides bearing O-methyl or O-sulfo groups at C-3 of the Gal residue: specific acceptors for Gal: 3-O-sulfotransferases.

R K Jain1, C F Piskorz, E V Chandrasekaran, K L Matta.   

Abstract

Our recent studies have revealed the existence of two distinct Gal: 3-O-sulfotransferases capable of acting on the C-3 position of galactose in a Core 2 branched structure, e.g., Galbeta1-->4GlcNAcbeta1-->6(Galbeta1-->3)GalNacalph a1-->OBenzyl as acceptor to give 3-O-sulfoGalbeta1-->4GlcNAcbeta1-->3(Galbeta1-->3)G alNAcalpha1-->OB 20 and Galbeta1-->4GlcNAcbeta1-->6(3-O-sulfoGalbeta1-->3)G alNAcalpha1-->OB 23. We herein report the synthesis of these two compounds and also that of other modified analogs that are highly specific acceptors for the two sulfotransferases. Appropriately protected 1-thio-glycosides 7, 8, and 10 were employed as glycosyl donors for the synthesis of our target compounds.

Entities:  

Mesh:

Substances:

Year:  1998        PMID: 10211700     DOI: 10.1023/a:1006977607394

Source DB:  PubMed          Journal:  Glycoconj J        ISSN: 0282-0080            Impact factor:   2.916


  15 in total

1.  Synthesis of oligosaccharides containing beta-D-Gal-(1-->3)-O-(6-O-sulfo-beta-D-GlcNAc) as a terminal unit.

Authors:  B G Huang; R K Jain; W A Tabaczynski; J L Alderfer; K L Matta
Journal:  Carbohydr Res       Date:  1998-09       Impact factor: 2.104

2.  6'-sulfated sialyl Lewis x is a major capping group of GlyCAM-1.

Authors:  S Hemmerich; S D Rosen
Journal:  Biochemistry       Date:  1994-04-26       Impact factor: 3.162

3.  Novel sulfated ligands for the cell adhesion molecule E-selectin revealed by the neoglycolipid technology among O-linked oligosaccharides on an ovarian cystadenoma glycoprotein.

Authors:  C T Yuen; A M Lawson; W Chai; M Larkin; M S Stoll; A C Stuart; F X Sullivan; T J Ahern; T Feizi
Journal:  Biochemistry       Date:  1992-09-29       Impact factor: 3.162

4.  Ovarian cancer alpha 1,3-L-fucosyltransferase. Differentiation of distinct catalytic species with the unique substrate, 3'-sulfo-N-acetyllactosamine in conjunction with other synthetic acceptors.

Authors:  E V Chandrasekaran; R K Jain; K L Matta
Journal:  J Biol Chem       Date:  1992-11-25       Impact factor: 5.157

5.  Characterization of the specificities of human blood group H gene-specified alpha 1,2-L-fucosyltransferase toward sulfated/sialylated/fucosylated acceptors: evidence for an inverse relationship between alpha 1,2-L-fucosylation of Gal and alpha 1,6-L-fucosylation of asparagine-linked GlcNAc.

Authors:  E V Chandrasekaran; R K Jain; R D Larsen; K Wlasichuk; K L Matta
Journal:  Biochemistry       Date:  1996-07-09       Impact factor: 3.162

6.  Specificity analysis of three clonal and five non-clonal alpha 1,3-L-fucosyltransferases with sulfated, sialylated, or fucosylated synthetic carbohydrates as acceptors in relation to the assembly of 3'-sialyl-6'-sulfo Lewis x (the L-selectin ligand) and related complex structures.

Authors:  E V Chandrasekaran; R K Jain; R D Larsen; K Wlasichuk; R A DiCioccio; K L Matta
Journal:  Biochemistry       Date:  1996-07-09       Impact factor: 3.162

7.  Complex-type N-linked oligosaccharides of gp120 from human immunodeficiency virus type 1 contain sulfated N-acetylglucosamine.

Authors:  A Shilatifard; R K Merkle; D E Helland; J L Welles; W A Haseltine; R D Cummings
Journal:  J Virol       Date:  1993-02       Impact factor: 5.103

8.  Synthesis of oligosaccharides containing the X-antigenic trisaccharide (alpha-L-Fucp-(1----3)-[beta-D-Galp-(1----4)]-beta-D-GlcpNAc) at their nonreducing ends.

Authors:  R K Jain; K L Matta
Journal:  Carbohydr Res       Date:  1992-03-16       Impact factor: 2.104

9.  Selectin ligands and tumor-associated carbohydrate structures: specificities of alpha 2,3-sialyltransferases in the assembly of 3'-sialyl-6-sialyl/sulfo Lewis a and x, 3'-sialyl-6'-sulfo Lewis x, and 3'-sialyl-6-sialyl/sulfo blood group T-hapten.

Authors:  E V Chandrasekaran; R K Jain; R D Larsen; K Wlasichuk; K L Matta
Journal:  Biochemistry       Date:  1995-03-07       Impact factor: 3.162

10.  Identification of a carbohydrate-based endothelial ligand for a lymphocyte homing receptor.

Authors:  Y Imai; M S Singer; C Fennie; L A Lasky; S D Rosen
Journal:  J Cell Biol       Date:  1991-06       Impact factor: 10.539

View more
  3 in total

1.  Reversible sialylation: synthesis of cytidine 5'-monophospho-N-acetylneuraminic acid from cytidine 5'-monophosphate with alpha2,3-sialyl O-glycan-, glycolipid-, and macromolecule-based donors yields diverse sialylated products.

Authors:  E V Chandrasekaran; Jun Xue; Jie Xia; Robert D Locke; Khushi L Matta; Sriram Neelamegham
Journal:  Biochemistry       Date:  2007-12-08       Impact factor: 3.162

2.  Characterization of distinct Gal:3-O-sulfotransferase activities in human tumor epithelial cell lines and of calf lymph node GlcNAc : 6-O-sulfotransferase activity.

Authors:  E V Chandrasekaran; R K Jain; J M Rhodes; R Chawda; C Piskorz; K L Matta
Journal:  Glycoconj J       Date:  1999-09       Impact factor: 2.916

3.  Novel interactions of complex carbohydrates with peanut (PNA), Ricinus communis (RCA-I), Sambucus nigra (SNA-I) and wheat germ (WGA) agglutinins as revealed by the binding specificities of these lectins towards mucin core-2 O-linked and N-linked glycans and related structures.

Authors:  E V Chandrasekaran; Jun Xue; Jie Xia; Siraj D Khaja; Conrad F Piskorz; Robert D Locke; Sriram Neelamegham; Khushi L Matta
Journal:  Glycoconj J       Date:  2016-06-18       Impact factor: 2.916

  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.