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

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.

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 1998-10, Vol.8 (19), p.2803-2808
Main Authors: Hanessian, S, Huynh, H K, Reddy, G V, McNaughton-Smith, G, Ernst, B, Kolb, H C, Magnani, J, Sweeley, C
Format: Article
Language:English
Subjects:
beta-Lactams - chemical synthesis
beta-Lactams - chemistry
beta-Lactams - metabolism
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
Structure-Activity Relationship
Substrate Specificity
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Description
Summary: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.
ISSN:0960-894X
DOI:10.1016/S0960-894X(98)00500-9