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| Names | |
|---|---|
| Preferred IUPAC name 1-aminocyclopentane-1-carboxylic acid | |
| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| DrugBank |
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| ECHA InfoCard | 100.000.132 |
| KEGG |
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| UNII | |
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| Properties | |
| 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) |
| 50 mg/mL | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | Irritant |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Cycloleucine is a non-proteinogenicamino acid. It could be classified as acyclopentane derivative ofnorleucine, having two hydrogen atoms less. The α-carbon atom is not a stereocenter. Cycloleucine is a non-metabolisable amino acid that specifically and reversiblyinhibits nucleic acidmethylation. It is widely used inbiochemical experiments.[2]
In 2007, a research study had shown that cycloleucine can lowerS-adenosyl methionine (SAM) levels in primary rat hepatocytes by inhibiting the conversion of5′-methylthioadenosine to SAM through the methionine salvage pathway. Cycloleucine treatment in conjunction with higher levels ofcytochrome P450 2E1 (CYP2E1) and lower SAM levels in pyrazole hepatocytes[clarification needed] had shown an increased amount of cellapoptosis when compared to control hepatocytes.[3]
In a 2015 study on the role ofN6-methyladenosine (m6A) demethylation onadipogenesis, researchers treated porcine adipocytes with increasing concentrations of cycloleucine. The researchers measured mRNA concentration of m6A using thedot blot method, and the results showed that cycloleucine increased adipocyte growth by blocking methylation by inhibiting m6A levels relative to the control adipocytes.[4]
A 2022 study showed that cycloleucine inhibits porcineoocyte and embryo development. Researchers cultured porcine oocytes and isolated cumulus cells from theircumulus cell complexes, after which the cells were cultured in vitro with cycloleucine in increasing concentrations. The samples were monitored underfluorescence microscopy, with the results showing positive relationship between cycloleucine concentration and decreased viability and survival rate for oocytes.[5]
