Mimicking the Binding Motifs Found in the Crystal Structures of Protein–Carbohydrate Complexes: An Aromatic Analogue of Serine or Threonine Side Chain Hydroxyl/Main Chain Amide
Authors:
- 22 June 2007
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 2007 (20) , 3271-3276
Abstract
An aromatic analogue of the side chain hydroxyl/main chain amide of Ser or Thr was used for the construction of artificial receptors for N‐acetylneuraminic acid (Neu5Ac), the most common occurring sialic acid. The acyclic receptors, incorporating only neutral recognition sites, are able to bind Neu5Ac with an overall binding constant β2 of 105 M–2 in a competitive solvent, such as water‐containing [D6]DMSO. Both receptors show remarkable selectivity for Neu5Ac over D‐glucuronic acid (GlcA).(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)Keywords
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