シクロロイシン、環状ロイシン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/07/15 02:01:03」(JST)

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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

^ Cycloleucine at Sigma-Aldrich
^ 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.

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English Journal

Microtubes with rectangular cross-section by self-assembly of a short β-peptide foldamer.

Kim J, Kwon S, Kim SH, Lee CK, Lee JH, Cho SJ, Lee HS, Ihee H.SourceInstitute for Basic Science, Department of Chemistry, KAIST, Daejeon 305-701, Korea.
Journal of the American Chemical Society.J Am Chem Soc.2012 Dec 26;134(51):20573-6. doi: 10.1021/ja3088482. Epub 2012 Dec 14.
In nature, complex and well-defined structures are constructed by the self-assembly of biomolecules. It has been shown that β-peptide foldamers can mimic natural peptides and self-assemble into three-dimensional molecular architectures thanks to their rigid and predictable helical conformation in s
PMID 23215019

Synthesis of highly functionalized fluorinated cispentacin derivatives.

Nonn M, Kiss L, Hänninen MM, Sillanpää R, Fülöp F.SourceInstitute of Pharmaceutical Chemistry, University of Szeged, HU-6720, Eötvös 6, Hungary.
Chemistry & biodiversity.Chem Biodivers.2012 Nov;9(11):2571-81. doi: 10.1002/cbdv.201200323.
Fluorinated highly functionalized cispentacin derivatives were synthetised starting from an unsaturated bicyclic β-lactam through C=C bond functionalization via the dipolar cycloaddition of a nitrile oxide, isoxazoline opening, and fluorination by OH/F exchange.Copyright © 2012 Verlag Helvetica Ch
PMID 23161635

Investigation of the molecular response to folate metabolism inhibition.

Carroll N, Hughes L, McEntee G, Parle-McDermott A.SourceNutritional Genomics Group, School of Biotechnology, Dublin City University Dublin 9, Ireland.
The Journal of nutritional biochemistry.J Nutr Biochem.2012 Nov;23(11):1531-6. doi: 10.1016/j.jnutbio.2011.10.006. Epub 2012 Mar 7.
We investigated the molecular response to folate metabolism inhibition by exposing human lymphoblast cell lines to the methionine adenosyltransferase inhibitor cycloleucine. We carried out microarray analysis on replicate control and exposed cells by examining 47,000 transcripts on the Affymetrix HG
PMID 22402366

Japanese Journal

Cycloleucine encephalopathy

Neuropathol. Appl. Neurol. 6, 349-360, 1980
NAID 30037278086

Inhibition of intestinal absorption of phenylalanine by phenylalaninol.

The Journal of Biochemistry 78(2), 269-275, 1975
NAID 130006879172

Inhibition of intestinal absorption of phenylalanine by phenylalaninol.

The Journal of Biochemistry 78(2), 269-275, 1975
NAID 130003539727

「環状ロイシン」

Cycloleucine
	IUPAC name 1-Amino-1-cyclopentanecarboxylic acid
	Other names 1-Aminocyclopentanecarboxylic acid
Identifiers
CAS number	52-52-8
PubChem	2901
ChemSpider	2798
DrugBank	DB04620
KEGG	C03969
ChEBI	CHEBI:40547
ChEMBL	CHEMBL295830
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) ; 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 ;
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
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references