326
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of Ganglioside Mimics for Binding Studies with Myelin‐Associated Glycoprotein (MAG)Footnote*

&
Pages 611-647 | Received 31 Jan 2005, Accepted 24 May 2005, Published online: 16 Aug 2006

References

  • Mukhopadhyay , G. , Doherty , P. , Walsh , F. S. , Crocker , P. R. and Filbin , M. T. 1994 . A novel role for myelin‐associated glycoprotein as an inhibitor of axonal regeneration . Neuron , 13 : 757 – 767 .
  • McKerracher , L. , David , S. , Jackson , D. L. , Kottis , V. , Dunn , R. J. and Braun , P. E. 1994 . Identification of myelin associated glycoprotein as a major myelin‐derived inhibitor of neurite growth . Neuron , 13 : 805 – 811 .
  • McKerracher , L. 2002 . Ganglioside rafts as MAG receptors that mediate blockade of axon growth . Proc. Natl. Acad. Sci. USA , 99 : 7811 – 7813 .
  • DeBellard , M.‐E. , Tang , S. , Mukhopadhyay , G. , Shen , Y.‐J. and Filbin , M. T. 1996 . Myelin‐associated glycoprotein inhibits axonal regeneration from a variety of neurons via interaction with a sialoglycoprotein . Mol. Cell. NeuroSci. , 7 : 89 – 101 .
  • Vyas , A. A. , Patel , H. V. , Fromholt , S. E. , Heffer‐Lauc , M. , Vyas , K. A. , Dang , J. , Schachner , M. and Schnaar , R. L. 2002 . Gangliosides are functional nerve cell ligands for myelin‐associated glycoprotein (MAG), an inhibitor of nerve regeneration . Proc. Natl. Acad. Sci. USA , 99 : 8412 – 8417 .
  • Tettamanti , G. , Bonali , F. , Marchesini , F. and Zambotti , V. 1973 . New procedure for the extraction, purification, and fractionation of brain gangliosides . Biochim. Biophys. Acta , 296 : 160 – 170 .
  • Vankar , Y. D. and Schmidt , R. R. 2000 . Glycosphingolipids . Chem. Soc. Rev. , 29 : 210 – 216 .
  • Collins , B. E. , Kiso , M. , Hasegawa , A. , Tropak , M. B. , Roder , J. C. , Crocker , P. R. and Schnaar , R. L. 1997 . Binding specificities of the sialoadhesin family of I‐type Lectins. Sialic acid linkage and substructure requirements for binding of myelin‐associated glycoprotein, Schwann cell myelin protein, and sialoadhesin . J. Biol. Chem. , 272 : 16889 – 16895 .
  • Collins , B. E. , Ito , H. , Sawada , N. , Ishida , H. , Kiso , M. and Schnaar , R. L. 1999 . Enhanced binding of the neural siglecs, myelin‐associated glycoprotein and Schwann cell myelin protein, to Chol‐1 (a ‐series) gangliosides and novel sulfated Chol‐1 analogs . J. Biol. Chem. , 274 : 37637 – 37643 .
  • Strenge , K. , Schauer , R. , Bovin , N. , Hasegawa , A. , Ishida , H. , Kiso , M. and Kelm , S. 1998 . Glycan specificity of myelin‐associated glycoprotein and sialoadhesin deduced from interactions with synthetic oligosaccharides . Eur. J. Biochem. , 258 : 677 – 685 .
  • Collins , B. E. , Yang , L. J.S. , Mukhopadhyay , G. , Filbin , M. T. , Kiso , M. , Hasegawa , A. and Schnaar , R. L. 1997 . Sialic acid specificity of myelin‐associated glycoprotein binding . J. Biol. Chem. , 272 : 1248 – 1252 .
  • Kelm , S. , Brossmer , R. , Isecke , R. , Gross , H.‐J. , Strenge , K. and Schauer , R. 1998 . Functional groups of sialic acids involved in binding to siglecs (sialoadhesins) deduced from interactions with synthetic analogs . Eur. J. Biochem. , 255 : 663 – 672 .
  • Sears , P. and Wong , C.‐H. 1999 . Kohlenhydratmimetika: ein neuer Lösungsansatz für das Problem derkohlenhydratvermittelten biologischen Erkennung . Angew. Chem. , 111 : 2447 – 2471 .
  • 1999 . Carbohydrate mimetics: a new strategy for tackling the problem of carbohydrate‐mediated biological recognition . Angew. Chem. Int. Ed. , 38 : 2301 – 2324 .
  • Dove , A. 2001 . The bittersweet promise of glycobiology . Nat. Biotechnol. , 19 : 913 – 917 .
  • Ritter , T. K. and Wong , C.‐H. 2001 . Kohlenhydrate in der Antibiotikaforschung: ein neuer Ansatz zur Resistenzbekämpfung . Angew. Chem. , 113 : 3616 – 3641 .
  • 2001 . Carbohydrate‐based antibiotics: a new approach to tackling the problem of resistance . Angew. Chem. Int. , 40 : 3508 – 3533 .
  • Bänteli , R. and Ernst , B. 2001 . Synthesis of sialyl lewis x mimics. Modifications of the 6‐position of galactose . Bioorg. Med. Chem. Lett. , 11 : 459 – 462 .
  • von Itzstein , M. , Wu , W. Y. , Kok , G. B. , Pegg , M. S. , Dyason , J. C. , Jin , B. , Phan Tho , V. , Smythe , M. L. , ;White , H. F. , Oliver , S. W. , Colman , P. M. , Varghese , J. N. , Ryan , D. M. , Woods , J. M. , Bethell , R. C. , Hotham , V. J. , Cameron , J. M. and Penn , C. R. 1993 . Rational design of potent sialidase‐based inhibitors of influenza virus replication . Nature , 363 : 418 – 423 .
  • Amann , F. , Schaub , C. , Müller , B. and Schmidt , R. R. 1998 . New potent sialyltransferase inhibitors—synthesis of donor and of transition‐state analogues of sialyl donor CMP‐Neu5Ac . Chem. Eur. J. , 4 : 1106 – 1115 .
  • Müller , B. , Schaub , C. and Schmidt , R. R. 1998 . Efficient sialyltransferase inhibitors based on the generation of transition‐state analogues of the sialyl donor . Angew. Chem. , 110 : 3021 – 3024 . Angew. Chem. Int. Ed. 1998, 37, 2893–2897
  • Bernardi , A. , Potenza , D. , Capelly , A. M. , Garcia‐Herrero , A. , Canada , F. J. and Jimenez‐Barbero , J. 2002 . Second generation mimics of ganglioside GM1 oligosaccharide: a three‐dimensional view of their interactions with bacterial enterotoxins by NMR and computational methods . Chem. Eur. J. , 8 : 4597 – 4612 .
  • Arosio , D. , Baretti , S. , Cattaldo , S. , Potenza , D. and Bernardi , A. 2003 . Ganglioside GM1 mimics: lipophilic substituents improve affinity for cholera toxin . Bioorg. Med. Chem. Lett. , 13 : 3831 – 3834 .
  • Janssen , S. 2004 . “ Dissertation ” . Universität Konstanz .
  • Kinzy , W. and Schmidt , R. R. 1987 . Muraminsäure als Glycosyldonor und –akzeptor . Liebigs Ann. Chem. , : 407 – 415 .
  • Pacak , J. and Cerny , M. 1963 . Preparation and structure of 4,6‐O‐benzylidene‐D‐galactopyranose . Collect. Czech. Chem. Commun. , 28 : 541 – 544 .
  • Duclos , R. I. 2001 . The total syntheses of D‐erythro‐sphingosine, N‐palmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog . Chem. Phys. Lipids , 111 : 111 – 138 .
  • Gros , E. G. and Denlofen , V. 1962 . Benzylidene derivatives of D‐galactose . Chem. Ind. , : 1502 – 1503 .
  • Padron , J. I. , Morales , E. Q. and Vazquez , J. T. 1998 . Alkyl galactopyranosides: rotational population dependence of the hydroxymethyl group on the aglycon and its absolute configuration and on the anomeric configuration . J. Org. Chem. , 63 : 8247 – 8258 .
  • Kitov , P. I. and Bindle , D. R. 2001 . Mild oxidative one‐pot allyl group cleavage . Org. Lett. , 3 : 2835 – 2838 .
  • Zimmermann , P. , Greilich , U. and Schmidt , R. R. 1990 . Total synthesis of a hexaosyl ceramide glycolipid acting as a receptor for macrophage‐migration inhibition factor . Tetrahedron Lett. , 31 : 1849 – 1852 .
  • Greilich , U. , Zimmermann , P. , Jung , K.‐H. and Schmidt , R. R. 1993 . Synthesis of the heptasaccharide moiety of ganglioside BGM 1 . Liebigs Ann. Chem. , : 859 – 864 .
  • Herzner , H. , Eberling , J. , Schultz , M. , Zimmer , J. and Kunz , H. 1998 . Oligosaccharide synthesis via electrophile‐induced activation of glycosyl‐N‐allylcarbamates . J. Carbohydr. Chem. , 17 : 759 – 776 .
  • Zemplén , G. and Pascu , E. 1929 . Saponification of acetylated sugars and related substances . Ber. Dtsch. Chem. Ges. , 62B : 1613 – 1614 .
  • Degerbeck , F. , Fransson , B. , Grehn , L. and Ragnarsson , U. 1993 . Synthesis of 15N‐labelled chiral Boc‐amino acids from triflates: enantiomers of leucine and phenylalanine . J. Chem. Soc. Perkin Trans. 1 , 1 : 11 – 14 .
  • Kolb , H. C. and Ernst , B. 1997 . Development of tools for the design of selectin antagonists . Chem. Eur. J. , 3 : 1571 – 1578 .
  • Bayley , H. , Standring , D. N. and Knowles , J. R. 1978 . Propane‐1,3‐dithiol: A selective reagent for the efficient reduction of alkyl and aryl azides to amines . Tetrahedron Lett. , 19 : 3633 – 3634 .
  • Mayer , T. G. 1996 . Dissertation. Universität Konstanz ,
  • Stauch , T. , Greilich , U. and Schmidt , R. R. 1995 . Synthesis of ganglioside GM1 via a GA1 intermediate . Liebigs Ann. , : 2101 – 2111 .
  • Schmidt , R. R. , Behrendt , M. and Toepfer , A. 1990 . Nitriles as solvents in glycosylation reactions—highly selective β‐glycoside synthesis . Synlett , : 694 – 697 .
  • Willams , D. R. and Sit , S.‐Y. 1984 . Total synthesis of (+)‐phyllanthocin . J. Am. Chem. Soc. , 106 : 2949 – 2954 .
  • Thoma , G. , Kinzy , W. , Bruns , C. , Patten , J. T. , Magnani , J. L. and Bänteli , R. 1999 . Synthesis and biological evaluation of a potent E‐selectin antagonist . J. Med. Chem. , 42 : 4909 – 4913 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.