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.
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]
UsesEdit
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]
^Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
^Hermann Römpp, Jürgen Falbe und Manfred Regitz: Römpp Lexikon Chemie, 9. Auflage, Georg Thieme Verlag, Stuttgart 1992.
^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.
^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
^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
^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.
August 31, 2023
norleucine, abbreviated, amino, acid, with, formula, co2h, systematic, name, this, compound, aminohexanoic, acid, compound, isomer, more, common, amino, acid, leucine, like, most, other, amino, acids, norleucine, chiral, white, water, soluble, solid, namespref. 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 a amino acids norleucine is chiral It is a white water soluble solid Norleucine NamesPreferred IUPAC name 2S 2 Aminohexanoic acidOther names Caprine GlycoleucineIdentifiersCAS Number 327 57 1 2S 3D model JSmol Interactive image3DMet B00369Beilstein Reference 1721748ChEBI CHEBI 36405ChemSpider 401917DrugBank DB04419ECHA InfoCard 100 009 512EC Number 210 462 7Gmelin Reference 464584KEGG C01933MeSH NorleucinePubChem CID 9475RTECS number RC6308000UNII 832C8OV84SCompTox Dashboard EPA DTXSID40861874InChI InChI 1S C6H13NO2 c1 2 3 4 5 7 6 8 9 h5H 2 4 7H2 1H3 H 8 9 Key LRQKBLKVPFOOQJ UHFFFAOYSA NSMILES CCCCC N C O OPropertiesChemical formula C 6H 13N O 2Molar mass 131 175 g mol 1Melting point 301 C 574 F 574 K decomposes 3 Solubility in water 16 g L at 23 C 1 Acidity pKa 2 39 carboxyl 9 76 amino 2 Related compoundsRelated 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 Y verify what is Y N Infobox references Contents 1 Occurrence 2 Uses 3 See also 4 ReferencesOccurrence EditTogether 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 a 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 EditIt 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 b peptide AbP 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 Ab peptides were completely negated 7 See also EditLeucines description of the isomers of leucine norvaline isomer of valine that has similar biochemistry to that of norleucine References Edit Sicherheitsdatenblatt Acros permanent dead link Dawson R M C et al Data for Biochemical Research Oxford Clarendon Press 1959 Hermann Rompp Jurgen Falbe und Manfred Regitz Rompp Lexikon Chemie 9 Auflage Georg Thieme Verlag Stuttgart 1992 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 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 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 Clementi ME amp 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 Retrieved from https en wikipedia org w index php title Norleucine amp oldid 1160684742, wikipedia, wiki, book, books, library,
