Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/03/14 19:15:46」(JST)

wiki en

Norleucine (abbreviated as Nle) is an amino acid with the formula CH₃(CH₂)₃CH(NH₂)CO₂H (nonzwitterionic formula). 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

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 experiments probing prebiotic synthesis of amino acids, norleucine and especially norvaline are formed.^[5]

§Uses

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

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

§References

^ Sicherheitsdatenblatt Acros.
^ 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 and 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.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. Amanita smithianaによるキノコ中毒 amanita smithiana mushroom poisoning
2. キノコ中毒のマネージメント management of mushroom poisoning
3. キノコ中毒の臨床症状および評価 clinical manifestations and evaluation of mushroom poisoning

English Journal

O-GlcNAcylation of protein kinase A catalytic subunits enhances its activity: a mechanism linked to learning and memory deficits in Alzheimer's disease.

Xie S1,2, Jin N1,2, Gu J1,2, Shi J1, Sun J1, Chu D1, Zhang L2, Dai CL2, Gu JH1, Gong CX2, Iqbal K2, Liu F1,2.
Aging cell.Aging Cell.2016 Feb 3. doi: 10.1111/acel.12449. [Epub ahead of print]
Alzheimer's disease (AD) is characterized clinically by memory loss and cognitive decline. Protein kinase A (PKA)-CREB signaling plays a critical role in learning and memory. It is known that glucose uptake and O-GlcNAcylation are reduced in AD brain. In this study, we found that PKA catalytic subun
PMID 26840030

The MHC Class I Cancer-Associated Neoepitope Trh4 Linked with Impaired Peptide Processing Induces a Unique Noncanonical TCR Conformer.

Hafstrand I1, Doorduijn EM2, Duru AD1, Buratto J1, Oliveira CC2, Sandalova T1, van Hall T3, Achour A4.
Journal of immunology (Baltimore, Md. : 1950).J Immunol.2016 Jan 22. pii: 1502249. [Epub ahead of print]
MHC class I downregulation represents a significant challenge for successful T cell-based immunotherapy. T cell epitopes associated with impaired peptide processing (TEIPP) constitute a novel category of immunogenic Ags that are selectively presented on transporter associated with Ag processing-defi
PMID 26800871

Targeting glutamine metabolism in multiple myeloma enhances BIM binding to BCL-2 eliciting synthetic lethality to venetoclax.

Bajpai R1, Matulis SM1, Wei C1, Nooka AK1, Von Hollen HE1, Lonial S1, Boise LH1, Shanmugam M1.
Oncogene.Oncogene.2015 Dec 7. doi: 10.1038/onc.2015.464. [Epub ahead of print]
Multiple myeloma (MM) is a plasma cell malignancy that is largely incurable due to development of resistance to therapy-elicited cell death. Nutrients are intricately connected to maintenance of cellular viability in part by inhibition of apoptosis. We were interested to determine if examination of
PMID 26640142

Japanese Journal

2Fa12 大腸菌6-diazo-5-oxo-L-norleucine耐性株の解析(遺伝子工学,一般講演)

林幹朗,田畑和彦
日本生物工学会大会講演要旨集 (63), 152, 2011-08-25
NAID 110008911412

AFM Observation of the Blocking of Step Motion Caused by L-Norleucine on (100) and (001) Faces of an L-Isoleucine Crystal

Kamei Toshimichi,Hasegawa Kazuhiro,Yokota Masaaki [他],DOKI Norihito,SHIMIZU Kenji
Journal of chemical engineering of Japan 42(4), 464-470, 2009-07-01
… The blocking of step motion on (100) and (001) faces of an L-isoleucine (L-Ile) crystal caused by the addition of an aqueous solution of L-norleucine (L-Nle) to the L-Ile solution was investigated using an atomic force microscope (AFM). …
NAID 10025306560

Development of a Method for the Determination of γ-Aminobutyric Acid in Foodstuffs

Ishikawa Akiko,Oka Hiroyuki,Hiemori Miki [他],YAMASHITA Hiromi,KIMOTO Masumi,KAWASAKI Hitoshi,TSUJI Hideaki
Journal of nutritional science and vitaminology 55(3), 292-295, 2009-06-01
… A method for the determination of γ-aminobutyric acid (GABA) in foodstuffs has been developed by combination of its dinitrophenylation and high-performance liquid chromatography (HPLC) using norleucine as an internal standard. …
NAID 10025971529

Related Pictures

★リンクテーブル★

拡張検索	「diazooxonorleucine」

「diazooxonorleucine」

Norleucine
Names
	IUPAC name (2S)-2-Aminohexanoic acid
	Other names Caprine; Glycoleucine
Identifiers
3DMet	B00369
Beilstein Reference	1721748
CAS Registry Number	327-57-1 (2S)
ChEBI	CHEBI:36405
ChemSpider	401917
DrugBank	DB04419
EC number	210-462-7
Gmelin Reference	464584
	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 ;
Jmol-3D images	Image
KEGG	C01933
MeSH	Norleucine
PubChem	9475
RTECS number	RC6308000
	SMILES CCCCC(N)C(O)=O ;
UNII	832C8OV84S
Properties
Molecular formula	C6H13NO2
Molar mass	131.17 g·mol−1
Melting point	301 °C (574 °F; 574 K) (decomposes)
Solubility in water	16 g/l at 23 °C
Acidity (pKa)	2.39 (carboxyl), 9.76 (amino)
Hazards
S-phrases	S36/37
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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
	verify (what is: /?)
	Infobox references

　　[★]

ジアゾオキソノルロイシン

[1] Sicherheitsdatenblatt Acros.

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

[R.C3.B6mpp-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 and 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.

匿名

検索

案内

案内

norleucine