Cycloleucine

Title: Cycloleucine
CAS Registry Number: 52-52-8
CAS Name: 1-Aminocyclopentanecarboxylic acid
Additional Names: ACPC
Manufacturers' Codes: CB-1639; NSC-1026
Molecular Formula: C6H11NO2
Molecular Weight: 129.16
Percent Composition: C 55.79%, H 8.58%, N 10.84%, O 24.77%
Literature References: Synthetic amino acid thought to act as a valine antagonist. Prepn: Zelinsky, Stadnikoff, Z. Physiol. Chem. 75, 350 (1911); Connors, Ross, J. Chem. Soc. 1960, 2119; Cremlyn, ibid. 1962, 3977; Sudo, Ichihara, Bull. Chem. Soc. Jpn. 36, 34 (1963). Manuf: NL 6607754 (1966 to Rohm & Haas), C.A. 67, 73159b (1967). Review: R. B. Ross et al., J. Med. Pharm. Chem. 3, 1 (1961). Immunopharmacology: Rosenthale et al., J. Pharmacol. Exp. Ther. 180, 501 (1972); Brambilla et al., Cancer Chemother. Rep. Part 1 56, 579 (1972).
Properties: Crystals from ethanol-water, mp 330° (dec). Soly in water approx 5 g/100 ml. Forms stable metal salts.
Melting point: mp 330° (dec)
Derivative Type: Hydrochloride
CAS Registry Number: 92398-48-6; 66146-62-1 (monohydrate)
Properties: Prismic crystals from water, mp 274° (dec). LD50 in mice, rats (mg/kg): 309, 290 orally; in rats (mg/kg): 340 i.v. (Ross).
Melting point: mp 274° (dec)
Toxicity data: LD50 in mice, rats (mg/kg): 309, 290 orally; in rats (mg/kg): 340 i.v. (Ross)
Use: Biological testing material for immunosuppressive properties in mice; for amino acid transport studies.
Cyclomethycaine Cyclonite Cyclonium Iodide Cyclooctyne Cyclopentadiene

Cycloleucine[1]
Cycloleucin.svg
Identifiers
CAS number 52-52-8
PubChem 2901
ChemSpider 2798 YesY
DrugBank DB04620
KEGG C03969 YesY
ChEMBL CHEMBL295830 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C6H11NO2
Molar mass 129.16 g/mol
Appearance white of beige crystalline flakes or powder
Density 1.207 g/mL
Melting point 320 °C; 608 °F; 593 K
Boiling point 256.1 °C; 493.0 °F; 529.2 K
Solubility in water 50 mg/mL
Hazards
Main hazards Irritant
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Cycloleucine is a non-proteinogenic amino acid. It could be classified as a cyclic derivate of norleucine, having two hydrogen atoms less. Leading structure is a cyclopentane-ring. The α-carbon atom is not a stereocenter.

Cycloleucine is a non-metabolisable amino acid and is a specific and reversible inhibitor of nucleic acid methylation, and as such is widely used in biochemical experiments.[2]