Work

Preorganization of the Bioactive Conformation of Sialyl LewisX Analogues Correlates with Their Affinity to E-Selectin

Year: 2001

Type: article

Abstract: It pays to be organized: Steric repulsion between fucose and the methyl substituent of the adjacent tetrahydropyran reduces the distance between galactose and fucose in the E-selectin antagonist 1 compared to the distance in closely related compounds that lack the methyl group. This effect causes a solution conformation of 1 that already resembles its conformation when bound to E-selectin and, thus, leads to a significantly improved bioactivity.

Source: Angewandte Chemie International Edition

DOI: 10.1002/1521-3773(20010518)40:10<1941::aid-anie1941>3.3.co;2-k

Authors: Gebhard Thoma, John L. Magnani, John T. Patton, Beat Ernst, Wolfgang Jahnke

Institutions: Novartis (Switzerland), University of Basel

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

OpenAlex ID: W4245791383

FWCI:

Cites:

Cited by: 1

Related to: 10