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'''Norleucine''' (abbreviated as '''Nle''') is an ] with the formula CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>CH(NH<sub>2</sub>)CO<sub>2</sub>H. A systematic name for this compound is 2-aminohexanoic acid.<ref>The use of the name norleucine is discouraged as it is a misnomer, given than nor is defined for an amino acid with one less methylene group than found in the proteinogenic form.{{cite journal | title = Nomenclature and Symbolism For Amino Acids and Peptides | journal = Pure and Applied Chemistry | volume = 56 | issue = 5 | pages = 595-624 | date = 1984}}</ref> The compound is an isomer of the more common amino acid ]. It is a white water soluble solid. | '''Norleucine''' (abbreviated as '''Nle''') is an ] with the formula CH<sub>3</sub>(CH<sub>2</sub>)<sub>3</sub>CH(NH<sub>2</sub>)CO<sub>2</sub>H (non]ic formula). A systematic name for this compound is 2-aminohexanoic acid.<ref>The use of the name norleucine is discouraged as it is a misnomer, given than nor is defined for an amino acid with one less methylene group than found in the proteinogenic form. {{cite journal | title = Nomenclature and Symbolism For Amino Acids and Peptides | journal = Pure and Applied Chemistry | volume = 56 | issue = 5 | pages = 595-624 | date = 1984}}</ref> The compound is an isomer of the more common amino acid ]. Like most other ]s, norleucine is ]. It is a white water soluble solid. | ||
==Occurrence== | ==Occurrence== | ||
Together with ], norleucine is found in small amounts in some bacterial strains. Its biosynthesis has been examined. In ]s probing prebiotic synthesis of amino acids, norleucine and especially norvaline are formed.<ref>Alvarez-Carreno, Claudia; Becerra, Arturo; Lazcano, Antonio "Norvaline and Norleucine May Have Been More Abundant Protein Components during Early Stages of Cell Evolution" Origins of Life and Evolution of Biospheres 2014, volume 43, 363-375. {{DOI|10.1007/s11084-013-9344-3}}</ref> | Together with ], norleucine is found in small amounts in some bacterial strains where its concentration can approach millimolar. Its ] has been examined. It arise via the action of 2-isopropylmalate synthase]] on ]. The incorporation of Nle into peptides reflects the imperfect selectivity of the associated ]. In ]s probing prebiotic synthesis of amino acids, norleucine and especially norvaline are formed.<ref>Alvarez-Carreno, Claudia; Becerra, Arturo; Lazcano, Antonio "Norvaline and Norleucine May Have Been More Abundant Protein Components during Early Stages of Cell Evolution" Origins of Life and Evolution of Biospheres 2014, volume 43, 363-375. {{DOI|10.1007/s11084-013-9344-3}}</ref> | ||
==Uses== | ==Uses== |
Revision as of 13:27, 31 July 2014
Names | |
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IUPAC name (2S)-2-Aminohexanoic acid | |
Other names
Caprine Glycoleucine | |
Identifiers | |
CAS Number |
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3D model (JSmol) | |
Beilstein Reference | 1721748 |
ChEBI | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.009.512 |
EC Number |
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Gmelin Reference | 464584 |
KEGG | |
MeSH | Norleucine |
PubChem CID | |
RTECS number |
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UNII | |
CompTox Dashboard (EPA) | |
InChI
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SMILES
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Properties | |
Chemical formula | C6H13NO2 |
Molar mass | 131.175 g·mol |
Melting point | 301 °C (decomposes) |
Solubility in water | 16 g/l at 23 °C |
Acidity (pKa) | 2.39 (carboxyl), 9.76 (amino) |
Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references |
Norleucine (abbreviated as Nle) is an amino acid with the formula CH3(CH2)3CH(NH2)CO2H (nonzwitterionic formula). A systematic name for this compound is 2-aminohexanoic acid. The compound is an isomer of the more common amino acid leucine. Like most other α-amino acids, norleucine is chiral. It is a white water soluble solid.
Occurrence
Together with norvaline, norleucine is found in small amounts in some bacterial strains where its concentration can approach millimolar. Its biosynthesis has been examined. It arise via the action of 2-isopropylmalate synthase]] on α-ketobutyrate. The incorporation of Nle into peptides reflects the imperfect selectivity of the associated aminoacyl-tRNA synthetase. In Miller–Urey experiments probing prebiotic synthesis of amino acids, norleucine and especially norvaline are formed.
Uses
It is nearly isosteric methionine, even it does not contain sulfur. For example norleucine has been used to probe the role of methionine in Amyloid-β peptide (AβP) the central constituent of senile plaques in Alzheimer's disease. A study showed that with the substitution of the methionine at the 35 position with norleucine the neurotoxic effects of the Aβ peptides were completely negated.
See also
- Leucines, description of the isomers of leucine
References
- Hermann Römpp, Jürgen Falbe und Manfred Regitz: Römpp Lexikon Chemie, 9. Auflage, Georg Thieme Verlag, Stuttgart 1992.
- Sicherheitsdatenblatt Acros.
- Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
- The use of the name norleucine is discouraged as it is a misnomer, given than nor is defined for an amino acid with one less methylene group than found in the proteinogenic form. "Nomenclature and Symbolism For Amino Acids and Peptides". Pure and Applied Chemistry. 56 (5): 595–624. 1984.
- Alvarez-Carreno, Claudia; Becerra, Arturo; Lazcano, Antonio "Norvaline and Norleucine May Have Been More Abundant Protein Components during Early Stages of Cell Evolution" Origins of Life and Evolution of Biospheres 2014, volume 43, 363-375. doi:10.1007/s11084-013-9344-3
- Moroder, Luis "Isosteric replacement of sulfur with other chalcogens in peptides and proteins" Journal of Peptide Science 2005, volume 11, 187-214. doi:10.1002/psc.654
- Clementi, ME and Misiti, F (2005 Nov). "Substitution of methionine 35 inhibits apoptotic effects of Abeta(31-35) and Abeta(25-35) fragments of amyloid-beta protein in PC12 cells". Med Sci Monit. 11 (11): BR381-5. PMID 16258386.
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