Literature DB >> 17572398

Synthesis of a C-linked hyaluronic acid disaccharide mimetic.

Zhong-Xu Ren1, Qiang Yang, Kenneth N Price, Tianniu Chen, Cara Nygren, John F C Turner, David C Baker.   

Abstract

The synthesis of a C-disaccharide that is designed as a mimetic for the repeating unit disaccharide of hyaluronic acid is described. The target compound was obtained via the SmI2-promoted coupling reaction of the sulfone, 2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1,2-dideoxy-1-pyridinylsulfonyl-beta-D-glucopyranose (6), and the aldehyde, p-methoxyphenyl 2,3-di-O-benzyl-4-deoxy-4-C-formyl-6-O-p-methoxybenzyl-beta-D-glucopyranoside (14).

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Year:  2007        PMID： 17572398      PMCID： PMC1989762          DOI： 10.1016/j.carres.2007.05.031

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN： 0008-6215            Impact factor:   2.104


  9 in total

1.  Preparation of C-1 Glycals via Olefin Metathesis. A Convergent and Flexible Approach to C-Glycoside Synthesis(1).

Authors:  Daniel Calimente; Maarten H. D. Postema
Journal:  J Org Chem       Date:  1999-03-19       Impact factor: 4.354

2.  Synthesis of two hyaluronan trisaccharides

Authors: 
Journal:  Org Lett       Date:  2000-05-04       Impact factor: 6.005

Review 3.  CD44 acts both as a growth- and invasiveness-promoting molecule and as a tumor-suppressing cofactor.

Authors:  P Herrlich; H Morrison; J Sleeman; V Orian-Rousseau; H König; S Weg-Remers; H Ponta
Journal:  Ann N Y Acad Sci       Date:  2000-06       Impact factor: 5.691

4.  Stereocontrolled Synthesis of alpha-C-Galactosamine Derivatives via Chelation-Controlled C-Glycosylation.

Authors:  Dominique Urban; Troels Skrydstrup; Jean-Marie Beau
Journal:  J Org Chem       Date:  1998-04-17       Impact factor: 4.354

5.  A new variant of glycoprotein CD44 confers metastatic potential to rat carcinoma cells.

Authors:  U Günthert; M Hofmann; W Rudy; S Reber; M Zöller; I Haussmann; S Matzku; A Wenzel; H Ponta; P Herrlich
Journal:  Cell       Date:  1991-04-05       Impact factor: 41.582

Review 6.  Hyaluronan promotes the malignant phenotype.

Authors:  Bryan P Toole
Journal:  Glycobiology       Date:  2002-03       Impact factor: 4.313

7.  Synthesis of hyaluronic acid-related di-, tri-, and tetra-saccharides having an N-acetylglucosamine residue at the reducing end.

Authors:  T M Slaghek; Y Nakahara; T Ogawa; J P Kamerling; J F Vliegenthart
Journal:  Carbohydr Res       Date:  1994-03-04       Impact factor: 2.104

8.  Use of 2-pyridyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-beta-D-glucopyranoside as a glycosyl donor and methyl iodide as an activator for the synthesis of 1,2-trans-linked saccharides.

Authors:  H B Mereyala; V R Gurijala
Journal:  Carbohydr Res       Date:  1993-04-07       Impact factor: 2.104

9.  Diastereocontrolled Synthesis of Carbon Glycosides of N-Acetylneuraminic Acid via Glycosyl Samarium(III) Intermediates.

Authors:  Iontcho R Vlahov; Petinka I Vlahova; Robert J Linhardt
Journal:  J Am Chem Soc       Date:  1997-02-12       Impact factor: 15.419
  9 in total

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