Synthesis of the Four Stereoisomers of 1‐Amino‐2‐(hydroxymethyl)cyclobutanecarboxylic Acid and Their Biological Evaluation as Ligands for the Glycine Binding Site of the NMDA Receptor

doi:10.1002/EJOC.200200673

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Synthesis of the Four Stereoisomers of 1‐Amino‐2‐(hydroxymethyl)cyclobutanecarboxylic Acid and Their Biological Evaluation as Ligands for the Glycine Binding Site of the NMDA Receptor

Published Jun 1, 2003 · Claus‐Juergen Koch, G. Höfner, K. Polborn

European Journal of Organic Chemistry

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Abstract

A synthesis of all four stereoisomers [(1S,2S)-, (1R,2R)-, (1S,2R)-, (1R,2S)-] of 1-amino-2-(hydroxymethyl)cyclobutanecarboxyclic acid is presented. The synthesis is based on the chiral glycine equivalent 1, employed in both enantiomeric forms. The key step involves the cyclization of the silyl-protected iodohydrins 5a−d to the corresponding spiro derivatives 6a−d with the aid of the phosphazenic base tBu-P4. The final compounds were found to display moderate potency as ligands for the glycine binding site of the NMDA receptor. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

Study Snapshot

The four stereoisomers of 1-amino-2-(hydroxymethyl)cyclobutanecarboxylic acid show moderate potency as ligands for the glycine binding site of the NMDA receptor.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Synthesis of the Four Stereoisomers of 1‐Amino‐2‐(hydroxymethyl)cyclobutanecarboxylic Acid and Their Biological Evaluation as Ligands for the Glycine Binding Site of the NMDA Receptor

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