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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
Author(s) -
Koch ClausJürgen,
Höfner G.,
Polborn Kurt,
Wanner Klaus Theodor
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200200673
Subject(s) - chemistry , hydroxymethyl , glycine , stereochemistry , enantiomer , nmda receptor , amino acid , chirality (physics) , receptor , biochemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
A synthesis of all four stereoisomers [(1 S ,2 S )‐, (1 R ,2 R )‐, (1 S ,2 R )‐, (1 R ,2 S )‐] 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 t Bu‐P 4 . 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)