Norleucine

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Norleucine
Names
Preferred IUPAC name
(2S)-2-Aminohexanoic acid
Other names
Caprine
Glycoleucine
Identifiers
3D model (
JSmol
)
3DMet
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).
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Norleucine (abbreviated as Nle) is an

chiral
. It is a white, water-soluble solid.

Occurrence

Together with

aminoacyl-tRNA synthetase. In Miller–Urey experiments probing prebiotic synthesis of amino acids, norleucine and especially norvaline are formed.[5]

Uses

It is nearly isosteric with

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

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

References

  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. doi:10.1351/pac198456050595
    .
  5. doi:10.1007/s11084-013-9344-3
  6. doi:10.1002/psc.654
  7. PMID 16258386
    .
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