関: isoleucine

WordNet

the 12th letter of the Roman alphabet (同)l
an essential amino acid found in proteins; isomeric with leucine

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lira(イタリアの貨幣単位リラ)
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/07/08 14:08:49」(JST)

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Isoleucine (abbreviated as Ile or I)^[1] is an α-amino acid with the chemical formula HO₂CCH(NH₂)CH(CH₃)CH₂CH₃. It is an essential amino acid, which means that humans cannot synthesize it, so it must be ingested. Its codons are AUU, AUC and AUA.

With a hydrocarbon side chain, isoleucine is classified as a hydrophobic amino acid. Together with threonine, isoleucine is one of two common amino acids that have a chiral side chain. Four stereoisomers of isoleucine are possible, including two possible diastereomers of L-isoleucine. However, isoleucine present in nature exists in one enantiomeric form, (2S,3S)-2-amino-3-methylpentanoic acid.

Biosynthesis

As an essential nutrient, it is not synthesized in the body, hence it must be ingested, usually as a component of proteins. In plants and microorganisms, it is synthesized via several steps, starting from pyruvic acid and alpha-ketoglutarate. Enzymes involved in this biosynthesis include:^[2]

Acetolactate synthase (also known as acetohydroxy acid synthase)
Acetohydroxy acid isomeroreductase
Dihydroxyacid dehydratase
Valine aminotransferase

Catabolism

Isoleucine is both a glucogenic and a ketogenic amino acid. After transamination with alpha-ketoglutarate the carbon skeleton can be converted into either Succinyl CoA, and fed into the TCA cycle for oxidation or converted into oxaloacetate for gluconeogenesis (hence glucogenic). It can also be converted into Acetyl CoA and fed into the TCA cycle by condensing with oxaloacetate to form citrate. In mammals Acetyl CoA cannot be converted back to carbohydrate but can be used in the synthesis of ketone bodies or fatty acids, hence ketogenic.

Biotin, sometimes referred to as Vitamin B7 or Vitamin H, is an absolute requirement for the full catabolism of isoleucine (as well as leucine). Without adequate biotin, the human body will be unable to fully break down isoleucine and leucine molecules.^[3] This can lead to numerous physiological issues (related to muscle maintenance and protein synthesis, lipid metabolism, and fatty acid metabolism) as well as cognitive issues resulting from general metabolic pathway failure and the irritating effects of hydroxyisovalerate, a byproduct of incomplete isoleucine catabolism. Isovaleric acidemia is an example of a disorder caused by incomplete catabolism of leucine.^{[citation needed]}

Nutritional Sources

Even though this amino acid is not produced in animals, it is stored in high quantities. Foods that have high amounts of isoleucine include eggs, soy protein, seaweed, turkey, chicken, lamb, cheese, and fish.^[4]

Isomers of isoleucine

Forms of Isoleucine
Common name:	isoleucine	D-isoleucine	L-isoleucine	DL-isoleucine	allo-D-isoleucine	allo-L-isoleucine	allo-DL-isoleucine
Synonyms:		(R)-Isoleucine	L(+)-Isoleucine	(R,R)-isoleucine		alloisoleucine
PubChem:	CID 791	CID 94206	CID 6306	CID 76551
EINECS number:	207-139-8	206-269-2	200-798-2		216-143-9	216-142-3	221-464-2
CAS number:	443-79-8	319-78-8	73-32-5		1509-35-9	1509-34-8	3107-04-8


L-isoleucine (2S,3S) and D-isoleucine (2R,3R)

L-allo-isoleucine (2S,3R) and D-allo-isoleucine (2R,3S)

Synthesis

Isoleucine can be synthesized in a multistep procedure starting from 2-bromobutane and diethylmalonate.^[5] Synthetic isoleucine was originally reported in 1905.^[6]

German chemist Felix Ehrlich discovered isoleucine in hemoglobin in 1903.

References

^ IUPAC-IUBMB Joint Commission on Biochemical Nomenclature. "Nomenclature and Symbolism for Amino Acids and Peptides". Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc. Retrieved 2007-05-17.
^ Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. ISBN 1-57259-153-6.
^ "Biotin & Detoxification Needs in Cognitively Delayed Adult - Metametrix Learning Center". Metametrix.com. Retrieved 2013-10-18.
^ [1], List is in order of highest to lowest of per 200 Calorie serving of the food, not volume or weight.
^ "dl-Isoleucine", Org. Synth., 1955 ; Coll. Vol. 3: 495
^ Bouveault and Locquin, Compt. rend., 141, 115 (1905).

External links

Food Sources of Isoleucine
Isoleucine and valine biosynthesis

UpToDate Contents

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English Journal

A dipeptide and an amino acid present in whey protein hydrolysate increase translocation of GLUT-4 to the plasma membrane in Wistar rats.

Morato PN, Lollo PC, Moura CS, Batista TM, Carneiro EM, Amaya-Farfan J.SourceUniversity of Campinas (UNICAMP), Faculty of Food Engineering (FEA), 13083-862 Campinas, São Paulo, Brazil. primorato@gmail.com
Food chemistry.Food Chem.2013 Aug 15;139(1-4):853-9. doi: 10.1016/j.foodchem.2012.12.062. Epub 2013 Jan 23.
Whey protein hydrolysate (WPH) is capable of increasing muscle glycogen reserves and of concentrating the glucose transporter in the plasma membrane (PM). The objective of this study was to determine which WPH components could modulate translocation of the glucose transporter GLUT-4 to the PM of ani
PMID 23561181

Synthesis of amino acid conjugates of tetrahydrocurcumin and evaluation of their antibacterial and anti-mutagenic properties.

Manjunatha JR, Bettadaiah BK, Negi PS, Srinivas P.SourceDepartment of Plantation Products, Spices and Flavour Technology, CSIR-Central Food Technological Research Institute, Mysore 570 020, India.
Food chemistry.Food Chem.2013 Aug 15;139(1-4):332-8. doi: 10.1016/j.foodchem.2013.01.081. Epub 2013 Feb 6.
Tetrahydrocurcumin (THC), the hydrogenated and stable form of curcumin, exhibits physiological and pharmacological activities similar to curcumin. A protocol has been developed for the synthesis of novel conjugates of THC with alanine (2a), isoleucine (2b), proline (2c), valine (2d), phenylalanine (
PMID 23561114

A single amino acid V4I substitution in VP1 attenuates virulence of very virulent infectious bursal disease virus (vvIBDV) in SPF chickens and increases replication in CEF cells.

Yu F, Ren X, Wang Y, Qi X, Song J, Gao Y, Qin L, Gao H, Wang X.SourceDivision of avian infectious diseases, State Key Laboratory of Veterinary Biotechnology, Harbin Veterinary Research Institute, Chinese Academy of Agricultural Sciences, Harbin 150001, PR China.
Virology.Virology.2013 Jun 5;440(2):204-9. doi: 10.1016/j.virol.2013.02.026. Epub 2013 Mar 26.
Infectious bursal disease virus (IBDV) is a birnavirus that causes immunosuppressive disease in chickens. The emergence of very virulent IBDV (vvIBDV) has brought new challenges for this disease. The molecular determinants for the high pathogenicity of vvIBDV are not fully understood. Previous studi
PMID 23537958

Japanese Journal

CYP94B3 activity against jasmonic acid amino acid conjugates and the elucidation of 12-O-beta-glucopyranosyl-jasmonoyl-L-isoleucine as an additional metabolite

Kitaoka Naoki,Kawaide Hiroshi,Amano Naruki,Matsubara Takuya,Nabeta Kensuke,Takahashi Kosaku,Matsuura Hideyuki
Phytochemistry 99, 6-13, 2014-03
… Oxidation of jasmonoyl-L-isoleucine at the C-12 position, which is catalyzed by cytochrome P450s CYP94B3 and CYP94C1, is thought to be one of the main inactivation pathways. … In this study, an additional function of CYP94B3 was elucidated, as well additional jasmonoyl-L-isoleucine metabolites being investigated. …
NAID 120005438228

Transaction : Photocatalytic Activity of Titanium Oxide Nano-Networks Fabricated through Organogel Route Using L-Isoleucine-Based Gelator (繊維学会創立70周年記念特集号) -- (英文特集)

Suzuki Masahiro,Kikuchi Masahiro,Hanabusa Kenji
繊維学会誌 70(9), 213-217, 2014
… Titanium oxide nano-networks, which have various crystal structures, were fabricated by the sol-gel polymerization in an organogel formed by L-isoleucine organogelator and their photocatalytic activities were evaluated by a methylene blue method. …
NAID 130004687323

85. 12位の水酸化から始まるジャスモン酸イソロイシンンの代謝に関する研究(口頭発表,植物化学調節学会第46回大会)

北岡直樹,松原卓也,宮澤吉郎,佐藤道大,瀬戸義哉,高橋公咲,和久田真司,川出洋,松井博和,鍋田憲助,松浦英幸
植物化学調節学会研究発表記録集 (46), 101, 2011-10-03
… It has been shown that 7-iso-jasmonyl-L-isoleucine (JA-Ile) is the bioactive form involved in the jasmonate-mediated signaling pathway. …
NAID 110008902494

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「イソロイシン」

L-Isoleucine
	IUPAC name Isoleucine
	Other names 2-Amino-3-methylpentanoic acid
Identifiers
CAS number	73-32-5
PubChem	791
ChemSpider	6067
UNII	04Y7590D77
DrugBank	DB00167
KEGG	D00065
ChEBI	CHEBI:58045
Jmol-3D images	Image 1
	SMILES CC[C@H](C)[C@@H](C(=O)O)N ;
	InChI InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1 ; Key: AGPKZVBTJJNPAG-WHFBIAKZSA-N InChI=1/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1; Key: AGPKZVBTJJNPAG-WHFBIAKZBB ;
Properties
Molecular formula	C6H13NO2
Molar mass	131.17 g mol−1
Supplementary data page
Structure and; properties	n, εr, etc.
Thermodynamic; data	Phase behaviour; Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
	Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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	Infobox references