関: L-serine、S、Ser

WordNet

a sweetish crystalline amino acid involved in the synthesis by the body of cysteine
the 19th letter of the Roman alphabet (同)s
an antibiotic that is especially active against the tubercle bacillus
any of various brown and yellow finches of parts of Europe

PrepTutorEJDIC

sulfurの化学記号 / {略}South[ern]

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/01/06 12:30:33」(JST)

wiki ja

[Wiki ja表示]

この項目では、アミノ酸について記述しています。アトリ科の野鳥については「セリン (鳥)」をご覧ください。

セリン (serine) とはアミノ酸の1つで、ヒドロキシメチル基を持つ。Ser あるいは S の略号で表され、IUPAC命名法に従うと 2-アミノ-3-ヒドロキシプロピオン酸である。セリシン（絹糸に含まれる蛋白質の一種）の加水分解物から1865年に初めて単離され、ラテン語で絹を意味する sericum からこの名がついた。構造は1902年に明らかになった。

極性無電荷側鎖アミノ酸に分類され、グリシンなどから作り出せるため非必須アミノ酸である。糖原性を持つ。酵素の活性中心において、求核試薬として機能している場合がある。

生合成

生体内では、解糖系の中間体である 3-ホスホグリセリン酸から、ホスホグリセリン酸デヒドロゲナーゼ (EC 1.1.1.95) 、ホスホセリンアミノトランスフェラーゼ (EC 2.6.1.52)、ホスホセリンホスファターゼ (EC 3.1.3.3) の働きにより合成される。

EC 1.1.1.95 3-phosphoglycerate + NAD⁺ → 3-phosphohydroxypyruvate + NADH + H⁺

EC 2.6.1.52 3-phosphonooxypyruvate + L-glutamate → O-phosphoserine + 2-oxoglutarate

EC 3.1.3.3 O-phosphoserine + H₂O → serine + phosphate

グリシンと可逆的に相互変換される関係にある。

機能

プリン、ピリミジン、システイン、（バクテリアでは）トリプトファンなどの生合成に関与するため、代謝において重要である。

酵素の部分構造に含まれ重要な役割を果たす。キモトリプシン、トリプシンなど多くの酵素の活性中心に存在することが示されている。いわゆる神経ガスや殺虫剤はアセチルコリンエステラーゼの活性中心のセリン残基に結合し、酵素反応を阻害することによって毒性を発揮することが知られている。神経伝達物質であるアセチルコリンがその役目を終えたあと、アセチルコリンエステラーゼがすぐに破壊して活性を失わせるが、これが作用しないと過剰のアセチルコリンが蓄積することになり、痙攣などの発作を誘発して死に至らしめる。

蛋白質の構成要素としては、側鎖のヒドロキシ基によってグリコシド結合を形成するという特徴を持つ。これは糖尿病の症状を説明する際に必要となることがある。真核生物におけるシグナル伝達の際にキナーゼによってリン酸化される3種のアミノ酸残基の1つである。リン酸化されたセリン残基はホスホセリンとよばれる。セリンプロテアーゼは典型的なタンパク質分解酵素である。

出典

^ Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
^ Weast, Robert C., ed. (1981), CRC Handbook of Chemistry and Physics (62nd ed.), Boca Raton, FL: CRC Press, p. C-512, ISBN 0-8493-0462-8 .

外部リンク

セリン - 「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]

Not to be confused with Sarin.

Serine (abbreviated as Ser or S)^[3] is an amino acid with the formula HO₂CCH(NH₂)CH₂OH. It is one of the proteinogenic amino acids. Its codons in the genetic code are UCU, UCC, UCA, UCG, AGU and AGC. By virtue of the hydroxyl group, serine is classified as a polar amino acid.

Occurrence and biosynthesis

(S)-Serine (left) and (R)-serine (right) in zwitterionic form at neutral pH

This compound is one of the naturally occurring proteinogenic amino acids. Only the L-stereoisomer appears naturally in proteins. It is not essential to the human diet, since it is synthesized in the body from other metabolites, including glycine. Serine was first obtained from silk protein, a particularly rich source, in 1865. Its name is derived from the Latin for silk, sericum. Serine's structure was established in 1902.^[4]

The biosynthesis of serine starts with the oxidation of 3-phosphoglycerate to 3-phosphohydroxypyruvate and NADH. Reductive amination of this ketone followed by hydrolysis gives serine. Serine hydroxymethyltransferase catalyzes the reversible, simultaneous conversions of L-serine to glycine (retro-aldol cleavage) and 5,6,7,8-tetrahydrofolate to 5,10-methylenetetrahydrofolate (hydrolysis).^[5]

This compound may also be naturally produced when UV light illuminates simple ices such as a combination of water, methanol, hydrogen cyanide, and ammonia, suggesting that it may be easily produced in cold regions of space.^[6]

Production

Industrially, L-serine is produced by fermentation, with an estimated 100-1000 tonnes per year produced.^[7] In the laboratory, racemic serine can be prepared from methyl acrylate via several steps:^[8]

Biological function

Metabolic

Cysteine synthesis from serine. Cystathionine beta synthase catalyzes the upper reaction and cystathionine gamma-lyase catalyzes the lower reaction.

Serine is important in metabolism in that it participates in the biosynthesis of purines and pyrimidines. It is the precursor to several amino acids including glycine and cysteine, and tryptophan in bacteria. It is also the precursor to numerous other metabolites, including sphingolipids and folate, which is the principal donor of one-carbon fragments in biosynthesis.

Structural role

Serine plays an important role in the catalytic function of many enzymes. It has been shown to occur in the active sites of chymotrypsin, trypsin, and many other enzymes. The so-called nerve gases and many substances used in insecticides have been shown to act by combining with a residue of serine in the active site of acetylcholine esterase, inhibiting the enzyme completely.

As a constituent (residue) of proteins, its side chain can undergo O-linked glycosylation, which may be functionally related to^{[clarification needed]} diabetes.

It is one of three amino acid residues that are commonly phosphorylated by kinases during cell signaling in eukaryotes. Phosphorylated serine residues are often referred to as phosphoserine.

Serine proteases are a common type of protease.

Signaling

D-Serine, synthesized in the brain by serine racemase from L-serine (its enantiomer), serves as both a neurotransmitter and a gliotransmitter by coactivating NMDA receptors, making them able to open if they then also bind glutamate. D-serine is a potent agonist at the glycine site of the NMDA-type glutamate receptor. For the receptor to open, glutamate and either glycine or D-serine must bind to it. In fact, D-serine is a more potent agonist at the glycine site on the NMDAR than glycine itself. D-serine was only thought to exist in bacteria until relatively recently; it was the second D amino acid discovered to naturally exist in humans, present as a signalling molecule in the brain, soon after the discovery of D-aspartate. Had D amino acids been discovered in humans sooner, the glycine site on the NMDA receptor might instead be named the D-serine site.^[9]

Gustatory sensation

Pure D-Serine is an off-white crystalline powder with a very faint funky or dirty aroma. L-Serine is sweet with minor umami and sour tastes at high concentration. D-Serine is sweet with an additional minor sour taste at medium and high concentrations.^[10]

References

^ Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
^ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-512. ISBN 0-8493-0462-8..
^ "Nomenclature and symbolism for amino acids and peptides (IUPAC-IUB Recommendations 1983)", Pure Appl. Chem. 56 (5): 595–624, 1984, doi:10.1351/pac198456050595.
^ "Serine". The Columbia Encyclopedia 6th ed.. encyclopedia.com. http://www.encyclopedia.com/topic/serine.aspx. Retrieved 22 October 2012.
^ 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.
^ Elsila, Jamie E.; Dworkin, Jason P.; Bernstein, Max P.; Martin, Mildred P.; Sandford, Scott A. (2007), "Mechanisms of Amino Acid Formation in Interstellar Ice Analogs", Astrophys. J. 660 (1): 911–18, Bibcode 2007ApJ...660..911E, doi:10.1086/513141
^ Karlheinz Drauz, Ian Grayson, Axel Kleemann, Hans-Peter Krimmer, Wolfgang Leuchtenberger, Christoph Weckbecker (2005), "Amino Acids", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a02_057.pub2
^ Carter, Herbert E.; West, Harold D. (1940), "dl-Serine", Org. Synth. 20: 81, http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0774; Coll. Vol. 3: 774.
^ Mothet, Jean-Pierre; Parent, Angèle T.; Wolosker, Herman; Brady, Roscoe O., Jr.; Linden, David J.; Ferris, Christopher D.; Rogawski, Michael A.; Snyder, Solomon H. (2000), "d-Serine is an endogenous ligand for the glycine site of the N-methyl-d-aspartate receptor", Proc. Natl. Acad. Sci. USA 97 (9): 4926–31, Bibcode 2000PNAS...97.4926M, doi:10.1073/pnas.97.9.4926, PMC 18334, PMID 10781100, http://www.pnas.org/cgi/pmidlookup?view=long&pmid=10781100.
^ http://www.springerlink.com/content/27074j4t2n508r7t/fulltext.html [Amino Acids. 2012 May 16. [Epub ahead of print] Gustatory sensation of L: - and D: -amino acids in humans. Kawai M, Sekine-Hayakawa Y, Okiyama A, Ninomiya Y.

UpToDate Contents

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1. 遺伝性感覚自律神経ニューロパチーhereditary sensory and autonomic neuropathies [show details]
…cause HSAN1 are associated with reduced activity of the enzyme serine palmitoyltransferase, which catalyzes the condensation of L-serine and palmitoyl-CoA . In addition, SPTLC1 mutations result in reduced …
2. ペプチドホルモンのシグナル伝達および調節peptide hormone signal transduction and regulation [show details]
…Receptor serine/threonine kinases such as transforming growth factor beta (TGF-beta) receptors contain a single transmembrane domain. Stimulation of these receptors activates endogenous serine/threonine…
3. 小頭症に対する臨床遺伝学的アプローチmicrocephaly a clinical genetics approach [show details]
…transfer RNA synthetase gene (RARS2) . Microcephaly due to mutations in calcium/calmodulin-dependent serine protein kinase (CASK, MIM ), an X-linked gene. CASK mutations cause microcephaly, optic atrophy, …
4. インスリン受容体の構造および機能structure and function of the insulin receptor [show details]
…sites is serine 1305 or 1306 in the C-terminus , and another is in the juxtamembrane region. Serine phosphorylation appears capable of inhibiting insulin signal transduction . Similarly, serine/threonine …
5. 複合免疫不全combined immunodeficiencies [show details]
…deficiency Ras homolog gene family member H (RHOH) deficiency Macrophage stimulating 1 (MST1, or serine threonine kinase 4, STK4) deficiency Interleukin 2-inducible T cell kinase (ITK) deficiency Major …

English Journal

Prognostic significance of Aurora-A expression in human bladder cancer.

Lei Y, Yan S, Ming-De L, Na L, Rui-Fa H.SourceTianjin Unode Laboratory of Basic Medical Urology, Tianjin Institute of Urology, Department of Urology, the Second Hospital of Tianjin Medical University, PR China.
Acta histochemica.Acta Histochem.2011 Sep;113(5):514-8. Epub 2010 Jul 2.
Aurora-A is an oncogenic serine/threonine kinase, which plays important roles in tumorigenesis, development and chemoresistance of human cancers. The aim of the study was to detect the expression of Aurora-A gene in bladder cancer tissues and analyze its association with prognosis of bladder cancer
PMID 20598352

Protein kinase C epsilon affects mitochondrial function through estrogen-related receptor alpha.

Lu N, Wang W, Liu J, Wong CW.SourceGuangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences, 190 Kai Yuan Avenue, Science Park, Guangzhou 510530, China.
Cellular signalling.Cell Signal.2011 Sep;23(9):1473-8. Epub 2011 May 9.
Members of the protein kinase C (PKC) family have been implicated in controlling cell proliferation, differentiation, and motility. Many of these processes are energy demanding. How PKCs affect mitochondrial function to regulate energy production is not well defined. Using an inhibitor Go6983 with
PMID 21596133

Japanese Journal

Zipper-interacting protein kinase modulates canonical Wnt/beta-catenin signaling through interacting with Nemo-like kinase and T-cell factor 4

Togi Sumihito,Ikeda Sumihito,Kamitani Sumihito,Nakasuji Sumihito,Sekine Sumihito,Muromoto Ryuta,Nanbo Asuka,Oritani Kenji,Kawai Taro,Akira Shizuo,Matsuda Tadashi
Journal of Biological Chemistry 286(21), 19170-19177, 2011-05
… Zipper-interacting protein kinase (ZIPK) is a widely expressed serine/threonine kinase that has been implicated in apoptosis and transcriptional regulation. …
NAID 120003005575

Effect of glycogen synthase kinase 3 β-mediated presenilin 1 phosphorylation on amyloid β production is negatively regulated by insulin receptor cleavage.

Maesako M,Uemura K,Kubota M,Hiyoshi K,Ando K,Kuzuya A,Kihara T,Asada M,Akiyama H,Kinoshita A
Neuroscience 177, 298-307, 2011-03-17
… Presenilin 1 (PS1), a causative molecule of familial Alzheimer's disease (AD), is known to be an unprimed substrate of glycogen synthase kinase 3 β (GSK3β) [Twomey and McCarthy (2006) FEBS Lett 580:4015-4020] and is phosphorylated at serine 353, 357 residues in its cytoplasmic loop region [Kirschenbaum et al. …
NAID 120002970866

Related Pictures

★リンクテーブル★

リンク元	「セリン」「SER」「Ser」「S」「L-serine」
拡張検索	「CDPdiacylglycerol-serine O-phosphatidyltransferase」「homoserine O-succinyltransferase」「L-serine diazoacetate」「phosphatidylserine」

「セリン」

Serine
	IUPAC name Serine
	Other names 2-Amino-3-hydroxypropanoic acid
Identifiers
CAS number	56-45-1 , 302-84-1 , 312-84-5 (D-isomer)
PubChem	617
ChemSpider	5736 (L-form) , 597
UNII	452VLY9402
EC-number	206-130-6
DrugBank	DB00133
ChEBI	CHEBI:17115
ChEMBL	CHEMBL11298
IUPHAR ligand	726
Jmol-3D images	Image 1
	SMILES C([C@@H](C(=O)O)N)O ;
	InChI InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1 ; Key: MTCFGRXMJLQNBG-REOHCLBHSA-N InChI=1/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7) ;
Properties
Molecular formula	C3H7NO3
Molar mass	105.09 g mol−1
Appearance	white crystals or powder
Density	1.603 g/cm3 (22 °C)
Melting point	246 °C decomp.
Solubility in water	soluble
Acidity (pKa)	2.21 (carboxyl), 9.15 (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

セリン
	IUPAC名 Serine
	別称 2-Amino-3-hydroxypropionic acid
識別情報
CAS登録番号	56-45-1 , 302-84-1 , 312-84-5
PubChem	617
ChemSpider	5736 (L-form) , 597
UNII	452VLY9402
EINECS番号	206-130-6
KEGG	C00065
ChEMBL	CHEMBL11298
IUPHARリガンド	726
	SMILES C([C@@H](C(=O)O)N)O;
	InChI InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1 ; Key: MTCFGRXMJLQNBG-REOHCLBHSA-N InChI=1/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7);
特性
化学式	C3H7NO3
モル質量	105.09 g mol−1
外観	white crystals or powder
密度	1.603 g/cm3 (22 ºC)
融点	246 °C（分解）
水への溶解度	soluble
酸解離定数 pKa	2.21 (カルボキシル基), 9.15 (アミノ基)
	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: serine, Ser, S
同: 2-アミノ-3-ヒドロキシプロピオン酸 2-amino-3-hydroxypropionic acid
関: アミノ酸

極性。無電荷。
ヒドロキシル基(hydroxyl group)を有する。
アラニンの側鎖にヒドロキシル基が付いた形をしている。
側鎖：

-CH2-OH

Kinaseの標的となり、リン酸イオンが結合する。

-CH2-O-H2PO3

「SER」

　　[★]

「Ser」

　　[★]

セリン

関: S、serine

同: セリン

「S」

　　[★]

「L-serine」

　　[★]

L-セリン

関: serine

「CDPdiacylglycerol-serine O-phosphatidyltransferase」

　　[★] CDPジアシルグリセロール・セリン-O-ホスファチジルトランスフェラーゼ

関: phosphatidylserine synthase

「homoserine O-succinyltransferase」

　　[★]

ホモセリン-O-サクシニルトランスフェラーゼ

「L-serine diazoacetate」

　　[★] L-セリンジアゾアセテート

「phosphatidylserine」

　　[★] ホスファチジルセリン

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

[2] Weast, Robert C., ed. (1981), CRC Handbook of Chemistry and Physics (62nd ed.), Boca Raton, FL: CRC Press, p. C-512, ISBN 0-8493-0462-8 .

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

[2] Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-512. ISBN 0-8493-0462-8..

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

[4] "Serine". The Columbia Encyclopedia 6th ed.. encyclopedia.com. http://www.encyclopedia.com/topic/serine.aspx. Retrieved 22 October 2012.

[5] 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.

[6] Elsila, Jamie E.; Dworkin, Jason P.; Bernstein, Max P.; Martin, Mildred P.; Sandford, Scott A. (2007), "Mechanisms of Amino Acid Formation in Interstellar Ice Analogs", Astrophys. J. 660 (1): 911–18, Bibcode 2007ApJ...660..911E, doi:10.1086/513141

[Ullmann-7] Karlheinz Drauz, Ian Grayson, Axel Kleemann, Hans-Peter Krimmer, Wolfgang Leuchtenberger, Christoph Weckbecker (2005), "Amino Acids", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a02_057.pub2

[8] Carter, Herbert E.; West, Harold D. (1940), "dl-Serine", Org. Synth. 20: 81, http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0774; Coll. Vol. 3: 774.

[9] Mothet, Jean-Pierre; Parent, Angèle T.; Wolosker, Herman; Brady, Roscoe O., Jr.; Linden, David J.; Ferris, Christopher D.; Rogawski, Michael A.; Snyder, Solomon H. (2000), "d-Serine is an endogenous ligand for the glycine site of the N-methyl-d-aspartate receptor", Proc. Natl. Acad. Sci. USA 97 (9): 4926–31, Bibcode 2000PNAS...97.4926M, doi:10.1073/pnas.97.9.4926, PMC 18334, PMID 10781100, http://www.pnas.org/cgi/pmidlookup?view=long&pmid=10781100.

[AAs-10] ttp://www.springerlink.com/content/27074j4t2n508r7t/fulltext.html [Amino Acids. 2012 May 16. [Epub ahead of print] Gustatory sensation of L: - and D: -amino acids in humans. Kawai M, Sekine-Hayakawa Y, Okiyama A, Ninomiya Y.

セリン

IUPAC名 Serine
別称 2-Amino-3-hydroxypropionic acid
識別情報
CAS登録番号	56-45-1 , 302-84-1, 312-84-5
PubChem	617
ChemSpider	5736 (L-form), 597
UNII	452VLY9402
EINECS番号	206-130-6
KEGG	C00065
ChEMBL	CHEMBL11298
IUPHARリガンド	726
SMILES C([C@@H](C(=O)O)N)O
InChI InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m0/s1 Key: MTCFGRXMJLQNBG-REOHCLBHSA-N InChI=1/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)
特性^[2]
化学式	C₃H₇NO₃
モル質量	105.09 g mol⁻¹
外観	white crystals or powder
密度	1.603 g/cm³ (22 ºC)
融点	246 °C（分解）
水への溶解度	soluble
酸解離定数 pK_a	2.21 (カルボキシル基), 9.15 (アミノ基)^[1]
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。

匿名

検索

案内

serine