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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
Author(s) -
Mazik Monika,
König Alexander
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700295
Subject(s) - chemistry , amide , side chain , threonine , serine , stereochemistry , sialic acid , molecular recognition , selectivity , molecule , biochemistry , organic chemistry , phosphorylation , catalysis , polymer
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 β 2 of 10 5 M –2 in a competitive solvent, such as water‐containing [D 6 ]DMSO. Both receptors show remarkable selectivity for Neu5Ac over D ‐glucuronic acid (GlcA).(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)