Literature DB >> 7795411

alpha 1,3-Fucosylation of branched blood group I-type oligo-(N-acetyllactosamino)glycans by human milk transferases is restricted to distal N-acetyllactosamine units: the resulting isomers are separated by WGA-agarose chromatography.

R Niemelä1, J Natunen, E Brotherus, A Saarikangas, O Renkonen.   

Abstract

A partially purified preparation of alpha 1,3-fucosyltransferase(s) from human milk was used to [14C]fucosylate oligosaccharides containing Gal beta 1-4GlcNAc units. Substitution of N-acetyllactosamine at position 3' with a beta-linked N-acetyl-glucosamine enhanced the reactivity of the acceptor, whereas similar substitution at position 6' was inhibitory. Thus, the trisaccharide GlcNAc beta 1-6Gal beta 1-4GlcNAc (5), the branched tetrasaccharide GlcNAc beta 1-3(GlcNAc beta 1-6)Gal beta 1-4GlcNAc (11) and the triply branched decasaccharide GlcNAc beta 1-3(GlcNAc beta 1-6)Gal beta 1-4GlcNAc beta 1-3[GlcNAc beta 1-3(GlcNAc beta 1-6)Gal beta 1-4GlcNAc beta 1-6]Gal beta 1-4GlcNAc (26) gave remarkably poor yields of alpha 1,3-fucosylated products in comparison to GlcNAc beta 1-3Gal beta 1-4GlcNAc (3). beta 1,4-Galactosyl derivatives of 5 and 11, however, gave good yields of alpha 1,3-fucosylated products, but the fucosylation was restricted to the distal N-acetyllactosamine units of Gal beta 1-4GlcNAc beta 1-6Gal beta 1-4GlcNAc (16), Gal beta 1-4GlcNAc beta 1-3(Gal beta 1-4GlcNAc beta 1-6)Gal beta 1-4GlcNAc (18) and also in Gal alpha 1-3Gal beta 1-4GlcNAc beta 1-3(Gal alpha 1-3Gal beta 1-4GlcNAc beta 1-6)Gal beta 1-4GlcNAc (22). Immobilized wheat germ agglutinin (WGA), possessing high affinity for 16 [1], revealed no affinity for the fucosylated derivative Gal beta 1-4(Fuc alpha 1-3)GlcNAc beta 1-6Gal beta 1-4GlcNAc (17). The isomeric heptasaccharides Gal beta 1-4(Fuc alpha 1-3)GlcNAc beta 1-3(Gal beta 1-4GlcNAc beta 1-6)Gal beta 1-4GlcNAc (19) and Gal beta 1-4GlcNAc beta 1-3[Gal beta 1-4(Fuc alpha 1-3)GlcNAc beta 1-6]Gal beta 1-4GlcNAc (20) were readily separated from each other on WGA agarose, and so were the isomeric nonasaccharides Gal alpha 1-3Gal beta 1-4(Fuc alpha 1-3)GlcNAc beta 1-3(Gal alpha 1-3Gal beta 1-4GlcNAc beta 1-6)Gal beta 1-4GlcNAc (23) and Gal alpha 1-3Gal beta 1-4GlcNAc beta 1-3[Gal alpha 1-3Gal beta 1-4(Fuc alpha 1-3)GlcNAc beta 1-6]Gal beta 1-4GlcNAc (24).

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Year:  1995        PMID： 7795411     DOI： 10.1007/bf00731866

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


  34 in total

1.  A role for sialyl Lewis-X/A glycoconjugates in capillary morphogenesis.

Authors:  M Nguyen; N A Strubel; J Bischoff
Journal:  Nature       Date:  1993-09-16       Impact factor: 49.962

2.  Oligosaccharides of human milk. Structural studies of two new octasaccharides, difucosyl derivatives of para-lacto-N-hexaose and para-lacto-N-neohexaose.

Authors:  K Yamashita; Y Tachibana; A Kobata
Journal:  J Biol Chem       Date:  1977-08-10       Impact factor: 5.157

3.  Expression of a carbohydrate signal, sialyl dimeric Le(x) antigen, is associated with metastatic potential of transitional cell carcinoma of the human urinary bladder.

Authors:  T Matsusako; H Muramatsu; T Shirahama; T Muramatsu; Y Ohi
Journal:  Biochem Biophys Res Commun       Date:  1991-12-31       Impact factor: 3.575

Review 4.  Structure and function of sphingoglycolipids in transmembrane signalling and cell-cell interactions.

Authors:  S Hakomori
Journal:  Biochem Soc Trans       Date:  1993-08       Impact factor: 5.407

5.  PADGEM-dependent adhesion of platelets to monocytes and neutrophils is mediated by a lineage-specific carbohydrate, LNF III (CD15).

Authors:  E Larsen; T Palabrica; S Sajer; G E Gilbert; D D Wagner; B C Furie; B Furie
Journal:  Cell       Date:  1990-11-02       Impact factor: 41.582

6.  CD62 and endothelial cell-leukocyte adhesion molecule 1 (ELAM-1) recognize the same carbohydrate ligand, sialyl-Lewis x.

Authors:  M J Polley; M L Phillips; E Wayner; E Nudelman; A K Singhal; S Hakomori; J C Paulson
Journal:  Proc Natl Acad Sci U S A       Date:  1991-07-15       Impact factor: 11.205

7.  The linear tetrasaccharide, Gal beta 1-4GlcNAc beta 1-6Gal beta 1-4GlcNAc, isolated from radiolabeled teratocarcinoma poly-N-acetyllactosaminoglycan resists the action of E. freundii endo-beta-galactosidase.

Authors:  O Renkonen; L Penttilä; A Makkonen; R Niemelä; A Leppänen; J Helin; A Vainio
Journal:  Glycoconj J       Date:  1989       Impact factor: 2.916

8.  ELAM-1 mediates cell adhesion by recognition of a carbohydrate ligand, sialyl-Lex.

Authors:  M L Phillips; E Nudelman; F C Gaeta; M Perez; A K Singhal; S Hakomori; J C Paulson
Journal:  Science       Date:  1990-11-23       Impact factor: 47.728

9.  Wheat germ agglutinin chromatography of GlcNac beta 1-3(GlcNAc beta 1-6)Gal and GlcNAc beta 1-3(GlcNAc beta 1-6)Gal beta 1-4GlcNAc, obtained by in vitro synthesis and by partial cleavage of teratocarcinoma poly-N-acetyllactosaminoglycans.

Authors:  A Seppo; L Penttilä; A Makkonen; A Leppänen; R Niemelä; J Jäntti; J Helin; O Renkonen
Journal:  Biochem Cell Biol       Date:  1990-01       Impact factor: 3.626

10.  Sialylation of glycoprotein oligosaccharides N-linked to asparagine. Enzymatic characterization of a Gal beta 1 to 3(4)GlcNAc alpha 2 to 3 sialyltransferase and a Gal beta 1 to 4GlcNAc alpha 2 to 6 sialyltransferase from rat liver.

Authors:  J Weinstein; U de Souza-e-Silva; J C Paulson
Journal:  J Biol Chem       Date:  1982-11-25       Impact factor: 5.157
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  2 in total

Review 1.  In vitro experimental studies of sialyl Lewis x and sialyl Lewis a on endothelial and carcinoma cells: crucial glycans on selectin ligands.

Authors:  R Renkonen; P Mattila; M L Majuri; J Räbinä; S Toppila; J Renkonen; L Hirvas; J Niittymäki; J P Turunen; O Renkonen; T Paavonen
Journal:  Glycoconj J       Date:  1997-08       Impact factor: 2.916

Review 2.  Human Milk Oligosaccharides (HMOS): Structure, Function, and Enzyme-Catalyzed Synthesis.

Authors:  Xi Chen
Journal:  Adv Carbohydr Chem Biochem       Date:  2015-11-11       Impact factor: 3.714
  2 in total

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