Structure via PubChem · Public domain (PubChem)
cycloleucine
Sign in to saveAlso known as 1-Amino-1-cyclopentanecarboxylic acid, 1-Amino-cyclopentanecarboxylic acid, 1-Aminocyclopentane-1-carboxylic acid, 1-Aminocyclopentanecarboxylate, 1-Aminocyclopentanecarboxylic acid, Amino-1-cyclopentanecarboxylic acid, Cyclo-leucine, Cycloleucin
Cycloleucine is a non-proteinogenic amino acid. It could be classified as a cyclopentane derivative of norleucine, having two hydrogen atoms less. The α-carbon atom is not a stereocenter. Cycloleucine is a non-metabolisable amino acid that specifically and reversibly inhibits nucleic acid methylation. It is widely used in biochemical experiments.
Chemical data
- Formula
- C6H11NO2
- Molecular weight
- 129.16 g/mol
- IUPAC name
- 1-aminocyclopentane-1-carboxylic acid
- SMILES
- C1CCC(C1)(C(=O)O)N
- InChIKey
- NILQLFBWTXNUOE-UHFFFAOYSA-N
- XLogP
- -2.6
- Polar surface area
- 63.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,409 papers- Cycloleucine encephalopathy.Neuropathology and applied neurobiology · 1980
- Cycloleucine negatively regulates porcine oocyte maturation and embryo development by modulating N6-methyladenosine and histone modifications.Theriogenology · 2022
- Transcriptome analysis of the inhibitory effect of cycloleucine on myogenesis.Poultry science · 2022
- Effects of exogenous glycine betaine and cycloleucine on photosynthetic capacity, amino acid composition, and hormone metabolism in Solanum melongena L.Scientific reports · 2023
- Cycloleucine blocks NMDA responses in cultured hippocampal neurones under voltage clamp: antagonism at the strychnine-insensitive glycine receptor.British journal of pharmacology · 1989
via PubMed
Wikidata facts
- Mass
- 129.079
Show 3 more facts
- chemical formula
- C₆H₁₁NO₂
- canonical SMILES
- C1CCC(C1)(C(=O)O)N
- Commons category
- Cycloleucine
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
1 sectionsContents
- References
Cycloleucine is a non-proteinogenic amino acid. It could be classified as a cyclopentane derivative of norleucine, having two hydrogen atoms less. The α-carbon atom is not a stereocenter. Cycloleucine is a non-metabolisable amino acid that specifically and reversibly inhibits nucleic acid methylation. It is widely used in biochemical experiments.
In 2007, a research study had shown that cycloleucine can lower S-adenosyl methionine (SAM) levels in primary rat hepatocytes by inhibiting the conversion of 5′-methylthioadenosine to SAM through the methionine salvage pathway. Cycloleucine treatment in conjunction with higher levels of cytochrome P450 2E1 (CYP2E1) and lower SAM levels in pyrazole hepatocytes had shown an increased amount of cell apoptosis when compared to control hepatocytes.
Excerpted from Wikipedia’s “cycloleucine” article, available under the CC BY-SA 4.0 licence.