Norleucine

Norleucine
Names
	IUPAC name (2S)-2-Aminohexanoic acid
	Other names Caprine; Glycoleucine
Identifiers
CAS Number	327-57-1 (2S);
3D model (JSmol)	Interactive image;
Beilstein Reference	1721748
ChEBI	CHEBI:36405;
ChemSpider	401917;
DrugBank	DB04419;
ECHA InfoCard	100.009.512
EC Number	210-462-7;
Gmelin Reference	464584
KEGG	C01933;
MeSH	Norleucine
PubChem CID	9475;
RTECS number	RC6308000;
UNII	832C8OV84S;
CompTox Dashboard (EPA)	DTXSID40861874 ;
	InChI InChI=1S/C6H13NO2/c1-2-3-4-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9) Key: LRQKBLKVPFOOQJ-UHFFFAOYSA-N;
	SMILES CCCCC(N)C(O)=O;
Properties
Chemical formula	C6H13NO2
Molar mass	131.175 g·mol−1
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 [77 °F], 100 kPa). verify (what is ?) Infobox references

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. It is a white water soluble solid.

Uses

It is nearly isosteric methionine, even it does not contain sulfur.^[5] 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.^[6]

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.
^ Isosteric replacement of sulfur with other chalcogens in peptides and proteins Quick View Full Text By Moroder, Luis From Journal of Peptide Science (2005), 11(4), 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. {{cite journal}}: Check date values in: |date= (help)CS1 maint: multiple names: authors list (link)

[Römpp-1] Hermann Römpp, Jürgen Falbe und Manfred Regitz: Römpp Lexikon Chemie, 9. Auflage, Georg Thieme Verlag, Stuttgart 1992.

[2] Sicherheitsdatenblatt Acros.

[3] Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.

[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.

[5] Isosteric replacement of sulfur with other chalcogens in peptides and proteins Quick View Full Text By Moroder, Luis From Journal of Peptide Science (2005), 11(4), 187-214. doi:10.1002/psc.654

[6] 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. {{cite journal}}: Check date values in: |date= (help)CS1 maint: multiple names: authors list (link)

[1]

[2]

[3]

[4]

[5]

[6]

Uses

See also

References