Cycloleucine

Cycloleucine^[1]

Names
IUPAC name 1-Amino-1-cyclopentanecarboxylic acid
Other names 1-Aminocyclopentanecarboxylic acid
Identifiers
CAS Number	52-52-8
ChEBI	CHEBI:40547
ChEMBL	ChEMBL295830
ChemSpider	2798
DrugBank	DB04620
Jmol interactive 3D	Image Image
KEGG	C03969
PubChem	2901
InChI InChI=1S/C6H11NO2/c7-6(5(8)9)3-1-2-4-6/h1-4,7H2,(H,8,9) Key: NILQLFBWTXNUOE-UHFFFAOYSA-N InChI=1/C6H11NO2/c7-6(5(8)9)3-1-2-4-6/h1-4,7H2,(H,8,9) Key: NILQLFBWTXNUOE-UHFFFAOYAN
SMILES C1CCC(C1)(C(=O)O)N O=C(O)C1(N)CCCC1
Properties
Chemical 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]

References

1. Cycloleucine at Sigma-Aldrich
2. M Caboche and JP Bachellerie (1977). "RNA methylation and control of eukaryotic RNA biosynthesis. Effects of cycloleucine, a specific inhibitor of methylation, on ribosomal RNA maturation". European Journal of Biochemistry 74 (1): 19–29. doi:10.1111/j.1432-1033.1977.tb11362.x. PMID 856572.