Norleucine

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 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.

  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.