Norleucine: Difference between revisions
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'''Norleucine''' (abbreviated as '''Nle''') is an isomer of [[leucine]], the α-[[amino acid]] 2-amino-hexanoic acid. It is not found in natural [[protein]]s. Norleucine is used in experimental studies of protein structure and function. It is structurally similar to [[methionine]], however it does not contain [[sulfur]]. 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<ref>Nomenclature and Symbolism For Amino Acids and Peptides. Pure and Applied Chemistry, Vol. 56, No. 5, pp.595-624, 1984.</ref> |
'''Norleucine''' (abbreviated as '''Nle''') is an isomer of [[leucine]], the α-[[amino acid]] 2-amino-hexanoic acid. It is not found in natural [[protein]]s. Norleucine is used in experimental studies of protein structure and function. It is structurally similar to [[methionine]], however it does not contain [[sulfur]]. 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.<ref>Nomenclature and Symbolism For Amino Acids and Peptides. Pure and Applied Chemistry, Vol. 56, No. 5, pp.595-624, 1984.</ref> As it is short, the systematic name is most appropriate. |
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| ⚫ | Norleucine's structural similarity to the naturally occurring amino acid [[methionine]], has been used to show the roll of [[methionine]] in [[Beta amyloid|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.<ref>Clementi, ME and Misiti, F: 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.'', Nov. 2005 [http://www.ncbi.nlm.nih.gov/pubmed/?term=Substitution+of+methionine+35+inhibits+apoptotic+effects+of+Abeta(31-35)+and+Abeta(25-35)+fragments+of+amyloid-beta+protein+in+PC12+cells.]</ref> |
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| ⚫ | Norleucine's structural similarity to the naturally occurring amino acid [[methionine]], has been used to show the roll of [[methionine]] in [[Beta amyloid|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. |
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== See also == |
== See also == |
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* [[Leucines]], description of the isomers of leucine |
* [[Leucines]], description of the isomers of leucine |
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==References== |
==References== |
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{{Reflist}} |
{{Reflist}} |
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[[Category:Amino acids]] |
[[Category:Amino acids]] |
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Revision as of 00:01, 11 July 2014
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| Names | |
|---|---|
| IUPAC name
(2S)-2-aminohexanoic acid
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| Other names
Caprine
Glycoleucine | |
| Identifiers | |
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3D model (JSmol)
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| 1721748 | |
| ChEBI | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.009.512 |
| EC Number |
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| 464584 | |
| KEGG | |
| MeSH | Norleucine |
PubChem CID
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| RTECS number |
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C6H13NO2 | |
| Molar mass | 131.175 g·mol−1 |
| Melting point | 301 °C (decomposes) [1] |
| 16 g/l at 23 °C [2] | |
| Acidity (pKa) | 2.39 (carboxyl), 9.76 (amino)[3] |
| Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Norleucine (abbreviated as Nle) is an isomer of leucine, the α-amino acid 2-amino-hexanoic acid. It is not found in natural proteins. Norleucine is used in experimental studies of protein structure and function. It is structurally similar to methionine, however it does not contain sulfur. 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.[4] As it is short, the systematic name is most appropriate.
Norleucine's structural similarity to the naturally occurring amino acid methionine, has been used to show the roll 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.[5]
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.
- ^ Nomenclature and Symbolism For Amino Acids and Peptides. Pure and Applied Chemistry, Vol. 56, No. 5, pp.595-624, 1984.
- ^ Clementi, ME and Misiti, F: 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., Nov. 2005 [1]
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