Second generation mimics of ganglioside GM1 as artificial receptors for cholera toxin: replacement of the sialic acid moiety.
In a program directed towards the design and synthesis of mimics of ganglioside GM1, the NeuAc recognition domain was replaced by simple hydroxy acids, and the affinity of the new ligands to the cholera toxin was determined by fluorescence spectroscopy. The (R)-lactic acid derivative 4 was found to display the highest affinity of the series (KD = 190 microM).
Bernardi
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A
Dipartimento di Chimica Organica e Industriale, Università di Milano, Italy. anna.bernardi@unimi.it
Carrettoni
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L
Ciponte
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AG
Monti
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D
Sonnino
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S
D002772:Cholera Toxin / Q000378:metabolism*; D005677:G(M1) Ganglioside / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D018716:Molecular Mimicry; D015394:Molecular Structure; D011956:Receptors, Cell Surface / Q000737:chemistry / Q000378:metabolism*; D012794:Sialic Acids / Q000737:chemistry; D013050:Spectrometry, Fluorescence
D011956:Receptors, Cell Surface; D012794:Sialic Acids; C023552:choleragen receptor; D005677:G(M1) Ganglioside; D002772:Cholera Toxin