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{{Chembox
{{Chembox
| ImageFile = L-Norleucin.svg
| ImageFile = L-Norleucin.svg
| ImageSize = 180px
| ImageSize = 180px
| IUPACName = (2''S'')-2-Aminohexanoic acid
| PIN = (2''S'')-2-Aminohexanoic acid
|OtherNames =
| OtherNames =
Caprine<br />
Caprine<br />
Glycoleucine
Glycoleucine
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo = 327-57-1
| CASNo = 327-57-1
| CASNo_Comment = (2''S'')
| CASNo_Comment = (2''S'')
| PubChem = 9475
| PubChem = 9475
| ChemSpiderID = 401917
| ChemSpiderID = 401917
| EINECS = 210-462-7
| EINECS = 210-462-7
| DrugBank = DB04419
| DrugBank = DB04419
| KEGG = C01933
| KEGG = C01933
| MeSHName = Norleucine
| MeSHName = Norleucine
| ChEBI = 36405
| ChEBI = 36405
| RTECS = RC6308000
| RTECS = RC6308000
| UNII = 832C8OV84S
| UNII = 832C8OV84S
| SMILES = CCCCC(N)C(O)=O
| SMILES = CCCCC(N)C(O)=O
| InChI = 1S/C6H13NO2/c1-2-3-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)
| InChI = 1S/C6H13NO2/c1-2-3-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)
| InChIKey = LRQKBLKVPFOOQJ-UHFFFAOYSA-N
| InChIKey = LRQKBLKVPFOOQJ-UHFFFAOYSA-N
| Beilstein = 1721748
| Beilstein = 1721748
| Gmelin = 464584
| Gmelin = 464584
| 3DMet = B00369}}
| 3DMet = B00369}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C=6 |H=13 |N=1 |O=2
| C=6 | H=13 | N=1 | O=2
| Appearance =
| Appearance =
| MeltingPtC = 301
| MeltingPt = 301 °C (decomposes) <ref name="Römpp">Hermann Römpp, Jürgen Falbe und Manfred Regitz: ''Römpp Lexikon Chemie'', 9. Auflage, Georg Thieme Verlag, Stuttgart 1992.</ref>
| MeltingPt_notes = (decomposes) <ref name="Römpp">Hermann Römpp, Jürgen Falbe und Manfred Regitz: ''Römpp Lexikon Chemie'', 9. Auflage, Georg Thieme Verlag, Stuttgart 1992.</ref>
| BoilingPt =
| BoilingPt =
| pKa=2.39 (carboxyl), 9.76 (amino)<ref>Dawson, R.M.C., et al., ''Data for Biochemical Research'', Oxford, Clarendon Press, 1959.</ref>
| pKa =2.39 (carboxyl), 9.76 (amino)<ref>Dawson, R.M.C., et al., ''Data for Biochemical Research'', Oxford, Clarendon Press, 1959.</ref>
| Solubility = 16 g/l at 23 °C <ref>[http://search.be.acros.com/msds?for=acros&sup=acros&lang=DE&search=22604&button=Show Sicherheitsdatenblatt Acros.]</ref>
| Solubility = 16 g/L at 23 °C <ref>[http://search.be.acros.com/msds?for=acros&sup=acros&lang=DE&search=22604&button=Show Sicherheitsdatenblatt Acros.]{{dead link|date=February 2018 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>
}}
}}
| Section7 = {{Chembox Hazards
|Section7={{Chembox Hazards
| Rphrases = 43
| GHSPictograms =
| GHSSignalWord =
| SPhrases = {{S36/37}}
| HPhrases = {{HPhrases|}}
| PPhrases = {{PPhrases|}}
| GHS_ref = <ref>GHS: [https://www.sigmaaldrich.com/product/SIAL/74560 Sigma-Aldrich 74560] 27-04-2021: "Not a hazardous substance or mixture according to Regulation (EC) No 1272/2008"</ref>
}}
}}
| Section8 = {{Chembox Related
|Section8={{Chembox Related
| Function = [[Aminoacid]]s
| OtherFunction_label = [[Aminoacid]]s
| OtherFunctn = [[Norvaline]] (2-amino-pentanoic)<br />[[Aminocaproic acid]] (6-amino-hexanoic)<br />[[Leucine]] (2-amino-4-methyl-pentanoic)<br />[[Isoleucine]] (2-amino-3-methyl-pentanoic)<br />[[Lysine]] (2,6-diamino-hexanoic)
| OtherFunction = [[Norvaline]] (2-amino-pentanoic)<br />[[Aminocaproic acid]] (6-amino-hexanoic)<br />[[Leucine]] (2-amino-4-methyl-pentanoic)<br />[[Isoleucine]] (2-amino-3-methyl-pentanoic)<br />[[Lysine]] (2,6-diamino-hexanoic)
| OtherCpds = [[Caproic acid]] (hexanoic)
| OtherCompounds = [[Caproic acid]] (hexanoic)
}}
}}
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 265148831}}
| verifiedrevid = 265148831}}


'''Norleucine''' (abbreviated as '''Nle''') is an [[amino acid]] 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[[zwitterion]]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 | doi=10.1351/pac198456050595}}</ref> The compound is an isomer of the more common amino acid [[leucine]]. Like most other [[α-amino acid]]s, norleucine is [[chiral]]. It is a white water soluble solid.
'''Norleucine''' (abbreviated as '''Nle''') is an [[amino acid]] 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 | doi=10.1351/pac198456050595| doi-access = free }}</ref> The compound is an isomer of the more common amino acid [[leucine]]. Like most other [[α-amino acid]]s, norleucine is [[chiral]]. It is a white, water-soluble solid.


==Occurrence==
==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 experiment]]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 [[norvaline]], norleucine is found in small amounts in some bacterial strains where its concentration can approach millimolar. Its [[biosynthesis]] has been examined. It arises 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 experiment]]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==
It is nearly isosteric with [[methionine]], even though it does not contain [[sulfur]].<ref>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}}</ref> For this reason, norleucine has been used to probe the role 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>{{cite journal | author = Clementi, ME and Misiti, F | title = Substitution of methionine 35 inhibits apoptotic effects of Abeta(31-35) and Abeta(25-35) fragments of amyloid-beta protein in PC12 cells | journal = Med Sci Monit. | date = Nov 2005 | volume = 11 | issue = 11 | pages = BR381-5 | pmid= 16258386}}</ref>
It is nearly isosteric with [[methionine]], even though it does not contain [[sulfur]].<ref>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}}</ref> For this reason, norleucine has been used to probe the role 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>{{cite journal |author1=Clementi, ME |author2=Misiti, F |name-list-style=amp | title = Substitution of methionine 35 inhibits apoptotic effects of Abeta(31-35) and Abeta(25-35) fragments of amyloid-beta protein in PC12 cells | journal = Med. Sci. Monit. | date = Nov 2005 | volume = 11 | issue = 11 | pages = BR381-5 | pmid= 16258386}}</ref>


== See also ==
== See also ==
Line 59: Line 63:
{{Reflist}}
{{Reflist}}


[[Category:Amino acids]]
[[Category:Alpha-Amino acids]]
[[Category:Non-proteinogenic amino acids]]
{{Non-proteinogenic amino acids}}

Latest revision as of 21:18, 17 September 2023

Norleucine
Names
Preferred IUPAC name
(2S)-2-Aminohexanoic acid
Other names
Caprine
Glycoleucine
Identifiers
3D model (JSmol)
1721748
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.009.512 Edit this at Wikidata
EC Number
  • 210-462-7
464584
KEGG
MeSH Norleucine
RTECS number
  • RC6308000
UNII
  • InChI=1S/C6H13NO2/c1-2-3-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)
    Key: LRQKBLKVPFOOQJ-UHFFFAOYSA-N
  • CCCCC(N)C(O)=O
Properties
C6H13NO2
Molar mass 131.175 g·mol−1
Melting point 301 °C (574 °F; 574 K) (decomposes) [3]
16 g/L at 23 °C [1]
Acidity (pKa) 2.39 (carboxyl), 9.76 (amino)[2]
Related compounds
Related Aminoacids
 Norvaline (2-amino-pentanoic)
Aminocaproic acid (6-amino-hexanoic)
Leucine (2-amino-4-methyl-pentanoic)
Isoleucine (2-amino-3-methyl-pentanoic)
Lysine (2,6-diamino-hexanoic)
Related compounds
 Caproic acid (hexanoic)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Norleucine (abbreviated as Nle) is an amino acid with the formula CH3(CH2)3CH(NH2)CO2H. A systematic name for this compound is 2-aminohexanoic acid.[4] 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

[edit]

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 arises 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.[5]

Uses

[edit]

It is nearly isosteric with methionine, even though it does not contain sulfur.[6] For this reason, 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.[7]

See also

[edit]
  • Leucines, description of the isomers of leucine
  • norvaline, isomer of valine that has similar biochemistry to that of norleucine.

References

[edit]
  1. ^ Sicherheitsdatenblatt Acros.[permanent dead link‍]
  2. ^ Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
  3. ^ Hermann Römpp, Jürgen Falbe und Manfred Regitz: Römpp Lexikon Chemie, 9. Auflage, Georg Thieme Verlag, Stuttgart 1992.
  4. ^ 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. doi:10.1351/pac198456050595.
  5. ^ 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
  6. ^ 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
  7. ^ Clementi, ME & Misiti, F (Nov 2005). "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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