Exploration of beta-turn scaffolding motifs as components of sialyl Le(X) mimetics and their relevance to P-selectin

S Hanessian; H K Huynh; G V Reddy; G McNaughton-Smith; B Ernst; H C Kolb; J Magnani; C Sweeley

doi:10.1016/s0960-894x(98)00500-9

Exploration of beta-turn scaffolding motifs as components of sialyl Le(X) mimetics and their relevance to P-selectin

Bioorg Med Chem Lett. 1998 Oct 6;8(19):2803-8. doi: 10.1016/s0960-894x(98)00500-9.

Authors

S Hanessian¹, H K Huynh, G V Reddy, G McNaughton-Smith, B Ernst, H C Kolb, J Magnani, C Sweeley

Affiliation

¹ Department of Chemistry, Université de Montréal, Centre-ville, Montréal, Québec, Canada.

PMID: 9873626
DOI: 10.1016/s0960-894x(98)00500-9

Abstract

Monocyclic and bicyclic lactam units representing beta-turn surrogates were incorporated into a sialyl Le(X) structure by replacement of the natural sugar components. Low micromolar activity was found in a new P-selectin binding assay.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Binding, Competitive
Carbohydrate Conformation
Carbohydrate Sequence
E-Selectin / metabolism
Indolizines / chemical synthesis*
Indolizines / chemistry
Indolizines / metabolism*
Molecular Sequence Data
Oligosaccharides / chemical synthesis*
Oligosaccharides / chemistry
Oligosaccharides / metabolism*
P-Selectin / metabolism*
Sialyl Lewis X Antigen
Structure-Activity Relationship
Substrate Specificity
beta-Lactams / chemical synthesis*
beta-Lactams / chemistry
beta-Lactams / metabolism*

Substances

E-Selectin
Indolizines
Oligosaccharides
P-Selectin
Sialyl Lewis X Antigen
beta-Lactams