WordNet

a colorless crystalline amino acid found in protein; occurs in the hydrolysates of certain proteins; an essential component of human nutrition
the 20th letter of the Roman alphabet (同)t

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tritiumの化学記号

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/11/25 10:46:53」(JST)

wiki ja

[Wiki ja表示]

トレオニン (threonine) はアミノ酸の一種で、側鎖にヒドロキシエチル基を持つ。読みの違いでスレオニンと表記されることも多い。略号は Thr または T。トレオースに構造が似ていることから命名された。

極性無電荷側鎖アミノ酸に分類される。必須アミノ酸の1つ。穀物中のトレオニン含量は比較的高いが、消化吸収が悪い。糖原性を持つ。

光学活性中心を2つ持つため4つの異性体がある。すなわち L-トレオニンには2つのジアステレオマーが存在するが、(2S,3R) 体のみが L-トレオニンと呼ばれる。(2S,3S) 体は天然にはほとんど存在せず、L-アロトレオニン (L-allo-threonine) と呼ばれる。

L-トレオニン(2S,3R) & D-トレオニン(2R,3S)

L-アロトレオニン(2S,3S) & D-アロトレオニン(2R,3R)

側鎖のヒドロキシ基にグリコシル化を受け、糖鎖を形成する。

トレオニンキナーゼの作用によりリン酸化され、ホスホトレオニンとなる。

トレオニンを多く含む食品としてカッテージチーズ、鶏肉、魚、肉、レンズマメが挙げられる。

生合成[編集]

ヒトはトレオニンを体内で作り出すことができないため、必須アミノ酸に分類される。一方、植物や大部分の微生物はアスパラギン酸から合成している。生合成の各段階は次のようなものである。まず、酵素アスパルトキナーゼがアスパラギン酸のβ-カルボキシル基をリン酸化する。次に β-アスパルテートセミアルデヒドデヒドロゲナーゼによって還元され、β-アスパルテートセミアルデヒドになる。これはトレオニン、メチオニン、リシンの生合成において重要な中間体である。これがホモセリンデヒドロゲナーゼ、ホモセリンキナーゼ、トレオニンシンターゼの作用によりトレオニンとなる。

出典[編集]

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

外部リンク[編集]

トレオニン(スレオニン) - 「健康食品」の安全性・有効性情報（国立健康・栄養研究所）

wiki en

[Wiki en表示]

Threonine (abbreviated as Thr or T)^[2] is an α-amino acid with the chemical formula HO₂CCH(NH₂)CH(OH)CH₃. Its codons are ACU, ACA, ACC, and ACG. This essential amino acid is classified as polar. Together with serine, threonine is one of two proteinogenic amino acids bearing an alcohol group (tyrosine is not an alcohol but a phenol, since its hydroxyl group is bonded directly to an aromatic ring, giving it different acid/base and oxidative properties). It is also one of two common amino acids that bear a chiral side chain, along with isoleucine.

The threonine residue is susceptible to numerous posttranslational modifications. The hydroxyl side-chain can undergo O-linked glycosylation. In addition, threonine residues undergo phosphorylation through the action of a threonine kinase. In its phosphorylated form, it can be referred to as phosphothreonine.

History[edit]

Threonine was discovered as the last of the 20 common proteinogenic amino acids in the 1930s by William Cumming Rose.

Stereoisomerism[edit]


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

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

Threonine is one of two proteinogenic amino acids with two chiral centers. Threonine can exist in four possible stereoisomers with the following configurations: (2S,3R), (2R,3S), (2S,3S) and (2R,3R). However, the name L-threonine is used for one single diastereomer, (2S,3R)-2-amino-3-hydroxybutanoic acid. The second stereoisomer (2S,3S), which is rarely present in nature, is called L-allo-threonine. The two stereoisomers (2R,3S)- and (2R,3R)-2-amino-3-hydroxybutanoic acid are only of minor importance.^{[citation needed]}

Biosynthesis[edit]

As an essential amino acid, threonine is not synthesized in humans, hence we must ingest threonine in the form of threonine-containing proteins. In plants and microorganisms, threonine is synthesized from aspartic acid via α-aspartyl-semialdehyde and homoserine. Homoserine undergoes O-phosphorylation; this phosphate ester undergoes hydrolysis concomitant with relocation of the OH group.^[3] Enzymes involved in a typical biosynthesis of threonine include:

aspartokinase
β-aspartate semialdehyde dehydrogenase
homoserine dehydrogenase
homoserine kinase
threonine synthase.

Threonine biosynthesis

Metabolism[edit]

Threonine is metabolized in two ways:

It is converted to pyruvate via threonine dehydrogenase. An intermediate in this pathway can undergo thiolysis with CoA to produce acetyl-CoA and glycine.
In humans, it is converted to α-ketobutyrate in a less common pathway via the enzyme serine dehydratase, and thereby enters the pathway leading to succinyl-CoA.

Sources[edit]

Foods high in threonine include cottage cheese, poultry, fish, meat, lentils, Black turtle bean^[4] and Sesame seeds.^[5]

Racemic threonine can be prepared from crotonic acid by alpha-functionalization using mercury(II) acetate.^[6]

References[edit]

^ Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
^ "Nomenclature and symbolism for amino acids and peptides (IUPAC-IUB Recommendations 1983)", Pure Appl. Chem. 56 (5), 1984: 595–624, doi:10.1351/pac198456050595 .
^ Lehninger, Albert L.; Nelson, David L.; Cox, Michael M. (2000), Principles of Biochemistry (3rd ed.), New York: W. H. Freeman, ISBN 1-57259-153-6 .
^ http://ndb.nal.usda.gov/ndb/foods/show/4632?fg=&man=&lfacet=&count=&max=&sort=&qlookup=&offset=&format=Full&new=
^ http://nutritiondata.self.com/
^ Carter, Herbert E.; West, Harold D. (1940), "dl-Threonine", Org. Synth. 20: 101 ; Coll. Vol. 3: 813 .

External links[edit]

Food Sources of Threonine
Threonine biosynthesis
CID 205
CID 6288

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Related Pictures

★リンクテーブル★

リンク元	「スレオニン」「T」「L-threonine」
拡張検索	「protein-serine-threonine kinase」「serine-threonine kinase」「serine-threonine phosphatase」「threonine-tRNA ligase」「phosphothreonine」

「スレオニン」

Threonine
	IUPAC name Threonine
	Other names 2-Amino-3-hydroxybutanoic acid
Identifiers
CAS number	80-68-2 , ; 72-19-5 (L-isomer)
PubChem	6288
ChemSpider	6051
EC number	201-300-6
DrugBank	DB00156
ChEBI	CHEBI:57926
ChEMBL	CHEMBL291747
Jmol-3D images	Image 1
	SMILES C[C@H]([C@@H](C(=O)O)N)O ;
	InChI InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1 ; Key: AYFVYJQAPQTCCC-GBXIJSLDSA-N InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1 ;
Properties
Molecular formula	C4H9NO3
Molar mass	119.12 g mol−1
Solubility in water	(H2O, g/dl) 10.6(30°),14.1(52°),19.0(61°)
Acidity (pKa)	2.63 (carboxyl), 10.43 (amino)
Supplementary data page
Structure and; properties	n, εr, etc.
Thermodynamic; data	Phase behaviour; Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

トレオニン
	IUPAC名 Threonine
	別称 2-Amino-3-hydroxybutanoic acid
識別情報
CAS登録番号	80-68-2 , ; 72-19-5 (L-isomer)
PubChem	6288
ChemSpider	6051
EINECS	201-300-6
KEGG	C00188
	SMILES C[C@H]([C@@H](C(=O)O)N)O;
	InChI InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1 ; Key: AYFVYJQAPQTCCC-GBXIJSLDSA-N InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1;
特性
化学式	C4H9NO3
モル質量	119.12 g mol−1
酸解離定数 pKa	2.63 (carboxyl), 10.43 (amino)
	特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

　　[★]

英: threonine Thr T
同: 2-アミノ-3-ヒドロキシ酪酸 2-amino-3-hydroxybutyric acid。L-トレオニン L-threonine
関: アミノ酸

極性。無電荷
ヒドロキシル基を有する。
セリンの側鎖で-CH2OHのうち、炭素に結合している-Hを-CH3に置き換えた形をしている。(-CH(CH3)-OH)

-CH(CH3)-OH

Kinaseの標的となり、リン酸イオンが結合する。

-CH(CH3)-O-H2PO3

「T」

　　[★]

「L-threonine」

　　[★]

L-スレオニン、L-トレオニン

関: threonine

「protein-serine-threonine kinase」

　　[★]

タンパク質セリンスレオニンキナーゼ、タンパク質セリントレオニンキナーゼ

関: serine kinase、serine-threonine kinase、serine-threonine protein kinase、threonine kinase

「serine-threonine kinase」

　　[★]

セリンスレオニンキナーゼ、セリントレオニンキナーゼ

関: protein-serine-threonine kinase、Ser-Thr kinase、serine kinase、serine-threonine protein kinase、threonine kinase

「serine-threonine phosphatase」

　　[★]

セリン・スレオニンホスファターゼ、セリン・トレオニンホスファターゼ

関: phosphoprotein phosphatase、protein phosphatase

「threonine-tRNA ligase」

　　[★]

スレオニンtRNAリガーゼ、トレオニンtRNAリガーゼ

関: threonyl-tRNA synthetase

「phosphothreonine」

　　[★]

リン酸化スレオニン、ホスホスレオニン、リン酸化トレオニン

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

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

[2] "Nomenclature and symbolism for amino acids and peptides (IUPAC-IUB Recommendations 1983)", Pure Appl. Chem. 56 (5), 1984: 595–624, doi:10.1351/pac198456050595 .

[3] Lehninger, Albert L.; Nelson, David L.; Cox, Michael M. (2000), Principles of Biochemistry (3rd ed.), New York: W. H. Freeman, ISBN 1-57259-153-6 .

[4] ttp://ndb.nal.usda.gov/ndb/foods/show/4632?fg=&man=&lfacet=&count=&max=&sort=&qlookup=&offset=&format=Full&new=

[5] ttp://nutritiondata.self.com/

[6] Carter, Herbert E.; West, Harold D. (1940), "dl-Threonine", Org. Synth. 20: 101 ; Coll. Vol. 3: 813 .

匿名

検索

案内

案内

threonine