Synthesis of 2-Hydroxymethylglutamic Acid and Congeners Thereof
Section: For Industry
Category(ies): CNS Disorders | Small Molecules
Reference #: KOAL426528
OTC Contact: David Humphry, Ph.D (Directory Information | Send a Message)
Description
L-Glutamate is one of the most abundant excitatory amino acid found in the mammalian brain. This amino acid acts on diverse glutamate receptors, including the metabotropic glutamate receptor family. Inventors at Georgetown have found that a 2-substituted L-glutamate annalogue is able to act as a relatively potent agonist of the group 2 receptor mGluR3 while functioning as a weak antagonist of mGluR2.
Applications
- Expedient route to hydroxymethyl glutamate (HMG) starting from D-serine.
- Route produces not only parent structures but its gamma-substituted analogues as well.
- Method based on a tandem Michael addition ring-closure protocol followed by a stereoselective alkylation reaction that takes place from the convex face of the bicycle.
Advantages
Stage of Development
Zhang, et al. "A Tandem Michael Addition Ring-Closure Route to the Metabotropic Receptor Ligand alpha-(Hydroxymethyl) glutamic Acid and Its Gamma-Alkylated Derivatives", J. Org Chem. 66:7555-7559, 2001.
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Relevant Publications
No references or resources available.
Patent Status
U.S. Patent #6,599,940
