Cycloleucine

Cycloleucine[1]
IUPAC name 1-Amino-1-cyclopentanecarboxylic acid
Other names 1-Aminocyclopentanecarboxylic acid
Identifiers
CAS number	52-52-8
PubChem	2901
ChemSpider	2798 Y
DrugBank	DB04620
KEGG	C03969 Y
ChEMBL	CHEMBL295830 Y
Jmol-3D images	Image 1 Image 2
SMILES C1CCC(C1)(C(=O)O)N O=C(O)C1(N)CCCC1
InChI InChI=1S/C6H11NO2/c7-6(5(8)9)3-1-2-4-6/h1-4,7H2,(H,8,9) Y Key: NILQLFBWTXNUOE-UHFFFAOYSA-N Y InChI=1/C6H11NO2/c7-6(5(8)9)3-1-2-4-6/h1-4,7H2,(H,8,9) Key: NILQLFBWTXNUOE-UHFFFAOYAN
Properties
Molecular formula	C6H11NO2
Molar mass	129.16 g/mol
Melting point	320 °C, 593 K, 608 °F
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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].

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.