Literature DB >> 1431600

Preparation of lyso-GM1 (II3Neu5AcGgOse4-long chain bases) by a one-pot reaction.

S Sonnino1, D Acquotti, G Kirschner, A Uguaglianza, L Zecca, F Rubino, G Tettamanti.   

Abstract

A simple procedure is described for preparing lyso-GM1, a GM1 derivative that lacks the fatty acid moiety, starting from GM1 ganglioside using a one-pot reaction. Ganglioside deacylation was carried out in KOH/propan-1-ol in the absence of oxygen. The yield of lyso-GM1 under optimal conditions (6 h, 90 degrees C, 0.2 N KOH, 1 mM GM1) was 54%. The chemical structure of lyso-GM1 was determined by 1H-NMR and FAB-MS analyses, thus proving that the acetamide groups of galactosamine and sialic acid units were not affected during the deacylation reaction.

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Year:  1992        PMID: 1431600

Source DB:  PubMed          Journal:  J Lipid Res        ISSN: 0022-2275            Impact factor:   5.922


  6 in total

1.  Synthesis of reference standards to enable single cell metabolomic studies of tetramethylrhodamine-labeled ganglioside GM1.

Authors:  E Andreas Larsson; Ulf Olsson; Colin D Whitmore; Rita Martins; Guido Tettamanti; Ronald L Schnaar; Norman J Dovichi; Monica M Palcic; Ole Hindsgaul
Journal:  Carbohydr Res       Date:  2006-10-07       Impact factor: 2.104

2.  Partial synthesis of ganglioside and lysoganglioside lipoforms as internal standards for MS quantification.

Authors:  Martin Gantner; Günter Schwarzmann; Konrad Sandhoff; Thomas Kolter
Journal:  J Lipid Res       Date:  2014-10-22       Impact factor: 5.922

3.  Use of a photoactivable GM1 ganglioside analogue to assess lipid distribution in caveolae bilayer.

Authors:  M Pitto; J Brunner; A Ferraretto; D Ravasi; P Palestini; M Masserini
Journal:  Glycoconj J       Date:  2000 Mar-Apr       Impact factor: 2.916

4.  A facile method for controlling the reaction equilibrium of sphingolipid ceramide N-deacylase for lyso-glycosphingolipid production.

Authors:  Feng-Tao Huang; Yun-Bin Han; Yan Feng; Guang-Yu Yang
Journal:  J Lipid Res       Date:  2015-06-30       Impact factor: 5.922

Review 5.  GM1 Ganglioside: Past Studies and Future Potential.

Authors:  Massimo Aureli; Laura Mauri; Maria Grazia Ciampa; Alessandro Prinetti; Gino Toffano; Cynthia Secchieri; Sandro Sonnino
Journal:  Mol Neurobiol       Date:  2015-03-12       Impact factor: 5.590

Review 6.  Synthesis of radioactive and photoactivable ganglioside derivatives for the study of ganglioside-protein interactions.

Authors:  Laura Mauri; Simona Prioni; Nicoletta Loberto; Vanna Chigorno; Alessandro Prinetti; Sandro Sonnino
Journal:  Glycoconj J       Date:  2004       Impact factor: 3.009

  6 in total

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