Cycloleucine

Chemical properties

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The Uses of Cycloleucine

Cycloleucine is a synthetic amino acid used in numerous biochemical transport studies

The Uses of Cycloleucine

NMDA receptor antagonist, inhibits nucleic acid methylation; adrenergic agonist

The Uses of Cycloleucine

Cycloleucine can be used as a building block to synthesize:

• Phosphonylmethylaminocyclopentane-1-carboxylic acid by reacting with paraformaldehyde and diethylphosphite via Kabachnik-Field′s reaction.
• Benzo[b]thiophene-2-carboxylic acid {1-[1-(R)-(3-morpholin-4-ylpropylcarbamoyl)-2-phenylethylcarbamoyl]cyclopentyl}-amide, (MEN14268) as potential tachykinin NK2 receptor antagonist.

What are the applications of Application

1-Aminocyclopentanecarboxylic acid is an NMDA receptor antagonist at the glycine site

Definition

ChEBI: A non-proteinogenic alpha-amino acid that is cyclopentane substituted at position 1 by amino and carboxy groups.

General Description

Cycloleucine is a nonmetabolizable amino acid widely used as a building block in peptide synthesis.

Purification Methods

Any Cl -or other anions are removed by stirring with a strong cation exchange resin (Amberlite IR-120), filtering, and washing with distilled H2O until the filtrate is free from the anion. The resin is then stirred overnight with 6N NH4OH, filtered, the filtrate is decolourised (charcoal) and evaporated to dryness in a vacuum. The residue is recrystallised from H2O/EtOH. Also crystallise it from aqueous EtOH. The hydrochloride has m 222-224o(dec). [Neelakantan & Hartung J Org Chem 23 967 1958, Connors & Ross J Chem Soc 2119 1960. O’Donnell et al. Synthesis 127 1984, Beilstein 14 IV 974.]