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 | Zendy

Mazik Monika | Zendy; König Alexander | Zendy

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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

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)

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