Synthesis and structural analysis of the anilides of glucuronic acid and orientation of the groups on the carbohydrate scaffolding

The synthesis of anilides derived from glucuronic acid is described. Secondary anilides had a Z configuration in the solid state and showed intramolecular and intermolecular hydrogen bonding. However, on the basis of NMR and IR studies, there was generally no evidence for the same hydrogen bonding i...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 70; no. 10; pp. 4096 - 4106
Main Authors: Tosin, M, O'Brien, C, Fitzpatrick, GM, Muller-Bunz, H, Glass, WK, Murphy, PV
Format: Journal Article
Language:English
Published: WASHINGTON Amer Chemical Soc 13.05.2005
Subjects:
Anilides - chemical synthesis
Anilides - chemistry
Anilides - metabolism
Carbohydrates - chemistry
Chemistry
Chemistry, Organic
Glucuronic Acid - chemical synthesis
Glucuronic Acid - chemistry
Glucuronic Acid - metabolism
Hydrogen Bonding
Models, Chemical
Physical Sciences
Science & Technology
Solutions - chemistry
CYCLIC PEPTIDE RHODOPEPTIN
DESIGN
PEPTIDOMIMETICS
MIMETICS
BETA-D-GLUCOSE
SUGAR-AMINO-ACID
COMBINATORIAL SYNTHESIS
BIOLOGICAL EVALUATION
CONFORMATIONAL-ANALYSIS
MOLECULAR DIVERSITY
ISSN:0022-3263, 1520-6904
Online Access:Get more information
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Summary:The synthesis of anilides derived from glucuronic acid is described. Secondary anilides had a Z configuration in the solid state and showed intramolecular and intermolecular hydrogen bonding. However, on the basis of NMR and IR studies, there was generally no evidence for the same hydrogen bonding in solution. Tertiary anilides showed a strong preference for the E configuration on the basis of NOE studies and molecular mechanics calculations. The alkylation of the secondary anilides induces a configurational switch that alters the orientation of the aromatic group with respect to the pyranose, which has relevance for presentation or orientation of pharmacophoric groups on carbohydrate scaffolds.
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo0501994