Cycloleucine

WHITE TO BEIGE CRYSTALLINE FLAKES OR POWDER
1-aminocyclopentanecarboxylic acid is a non-proteinogenic alpha-amino acid that is cyclopentane substituted at position 1 by amino and carboxy groups. It has a role as an EC 2.5.1.6 (methionine adenosyltransferase) inhibitor.|Cycloleucine is non-metabolisable amino acid formed by cyclization of leucine. It is also a specific and reversible inhibitor of nucleic acid methylation and widely used in biochemical experiments.|Cycloleucine is a non-metabolizable synthetic amino acid, formed through the cyclization of the amino acid leucine, with immunosuppressive, antineoplastic, and cytostatic activities. Cycloleucine competitively inhibits the enzyme methionine adenosyltransferase, resulting in the inhibition of S-adenosylmethionine (SAM) synthesis from methionine and ATP, and subsequent nucleic acid methylation and polyamine production; RNA, and perhaps to a lesser extent, DNA biosyntheses and cell cycle progression are finally disrupted. This agent is also a competitive inhibitor at the glycine modulatory site of the N-methyl-D-aspartate (NMDA) receptor.|An amino acid formed by cyclization of leucine. It has cytostatic, immunosuppressive and antineoplastic activities.
ChEBI: A non-proteinogenic alpha-amino acid that is cyclopentane substituted at position 1 by amino and carboxy groups.
Cycloleucine is a nonmetabolizable amino acid widely used as a building block in peptide synthesis.
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.]