酪氨酸

酪氨酸
	IUPAC名; (S)-Tyrosine
别名	L-2-Amino-3-(4-hydroxyphenyl)propanoic acid
识别
CAS号	60-18-4（(L)）
PubChem	1153
ChemSpider	5833
SMILES	N[C@@H](Cc1ccc(O)cc1)C(O)=O;
ChEBI	58315
DrugBank	DB03839
性质
化学式	C9H11NO3
摩尔质量	181.19 g·mol−1
危险性
NFPA 704	1 1 0
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

酪氨酸（Tyrosine, 缩写为 Tyr or Y）^[1] 或 4 - 羟基苯丙氨酸, 是细胞用来合成蛋白质的22种胺基酸之一，在细胞中可用于合成蛋白质，其密码子为UAC和UAU，属于含有极性侧基，人体可自行合成的非必需胺基酸。单词“酪氨酸”是来自希腊语 tyros，意思奶酪。19世纪初被德国的化学家尤斯图斯·冯·李比希首先在起司的酪蛋白中发现，^[2]^[3] ，当用作于官能基或侧基时则称做酪氨酰。

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除了是一个蛋白质氨基酸，在蛋白质中的讯号传导过程中，酪氨酸凭借著酚官能基具有特殊作用，其功能为被蛋白激酶（所谓的酪氨酸激酶受体）信号转移的磷酸基的受器，而羟基的磷酸化改变的目标蛋白质的活性。

酪氨酸在光合作用中也扮演重要角色，在叶绿体（光系统II）中，在氧化叶绿素的还原反应中被当作电子提供者，使其进行酚醛OH-基团的去质子化，最后在光系统II中被四个核心锰簇还原。

酪氨酸可在体内由苯丙氨酸合成，可在许多高蛋白质食品如如鸡，火鸡，鱼，牛奶，酸奶，奶酪，干酪，花生，杏仁，南瓜籽，芝麻，大豆，利马豆，鳄梨和香蕉中被发现。^[4]

在微生物或植物中，酪氨酸透过预苯酸（一种莽草酸反应途径产生的中间产物）产生，预苯酸被保留的羟基氧化脱羧得到对-羟基苯基丙酮酸，酪氨酸和α-酮戊二酸利用谷氨酸作为氮源进行氨基转移反应产生对-羟基苯基丙酮酸。

哺乳动物利用来自食物的必需氨基酸苯丙氨酸（PHE）来合成酪氨酸，苯丙胺酸转换成酪氨酸的反应由丙氨酸羟化酶（一种单氧化酶）催化而成，这种酶催化反应造成羟基和苯丙氨酸的6-碳环的芳香环端部的加成反应，使之变成酪氨酸。

磷酸化和硫酸盐化

某些酪氨酸可以用蛋白激酶的磷酸基标注，酪氨酸在磷酸化形式时被称作磷酸酪氨酸，酪氨酸磷酸化被认为是信号转导和酶活性调控中的关键步骤之一，磷酸酪氨酸可以被特定抗体所侦测，酪氨酸也可以被添加的硫酸基修饰，这个反应过程称为酪氨酸硫酸盐化^[5] 酪氨酸硫酸盐化是由酪氨酰蛋白质中的磺基转移酶（TPST）所催化而成，如同上面所提到的磷酸酪氨酸抗体，此抗体具有特异性可侦测到磺基酪氨酸。

神经传递物质和激素的前驱物

在大脑中的多巴胺细胞中，酪氨酸首先被限速酶酪氨酸羟化酶（TH）转化成左旋多巴 (L-DOPA)，再被转化为神经传递物质多巴胺。多巴胺可以被进一步转化成儿茶酚胺类物质去甲肾上腺素（NA）和肾上腺素。^[6]

甲状腺激素三碘甲状腺氨酸 (T₃)和在甲状腺胶体中的甲状腺素 (T₄)也来自于酪氨酸。^[6]

生物碱的前驱物

罂粟科催眠物质中的胶乳又称为罂粟，已被证实能将酪氨酸转换成生物碱吗啡，在其生物合成反应途径中，酪氨酸利用碳-14放射性标记的酪氨酸追踪体内合成路径。^{[来源请求]}

三甲氧苯乙胺生产仙人掌生物合成酪氨酸。 ^[7]

天然酚类的前驱物

酪氨酸解氨酶（TAL）是一种在天然酚生物合成反应途径中的酶，此酶将左旋酪氨酸转换成对香豆酸。

色素的前驱物

酪氨酸也是色素中的黑色素的前驱物。

降解作用

左旋酪氨酸（对-羟基苯丙氨酸）的分解作用，为酪氨酸转氨酶变成对-羟基苯基丙酮酸的α-酮戊二酸的依赖性转移反应而成，其结合位置为对位，缩写为p，表示苯环上的羟基和侧链是对面方位（见下图）。

下一步的氧化步骤中，由对-羟基苯基丙酮酸-双加氧酶和二氧化碳尿黑酸（2,5-二羟基苯基-1-乙酸乙酯）裂断催化而成，为了拆开尿黑酸的芳香环，通过氧分子进一步的结合以得到尿黑酸加氧酶是必须。

富马酰乙酸经由氧化的羟基所造成的羧基旋转，而产生maleylacetoacetate -顺式-反式异构酶。含有谷胱甘肽的顺-反异构酶作为辅酶，经由添加水分子，延胡索酰乙酰乙酸最终被延胡索酰乙酰乙酸水解酶给裂断。

富马酸盐（也是柠檬酸循环的代谢产物）和乙酰乙酸酯（3-丁酮酸）为游离状态，乙酰乙酸酯是一种酮，其被琥珀酰-CoA活化后可以被转化成乙酰-CoA，反过来又可被柠檬酸循环氧化或用于脂肪酸合成。

Phloretic酸也是大鼠中泌尿代谢物的酪氨酸。^[8]

已知左旋酪氨酸的三种结构异构物，除了常见的对位异构物左旋酪氨酸（对-酪氨酸或4-羟基苯丙氨酸）之外，另有两个区域异构物称为间位酪氨酸（间-酪氨酸，3-羟基苯丙氨酸或LM-酪氨酸）和邻位酪氨酸（邻-酪氨酸或2-羟基苯丙氨酸），两者皆自然存在，间-酪氨酸和邻-酪氨酸皆为罕见的，须经由苯丙氨酸的氧化压力条件下进行的非酶自由基羟化增加数量。^[9]^[10]

间-酪氨酸及其类似物（在自然中罕见但可以人工合成）在帕金森氏症，阿兹海默症和关节炎皆有所应用。^[11]

酪氨酸为神经传递物质和增加血浆神经传递物质程度（尤其是多巴胺和去甲肾上腺素）的前驱物，^[12]副作用为易对情绪造成影响，^[13]^[14]^[15]使在压力状况下对情绪的影响更为明显。

许多研究发现在压力，寒冷，疲劳，^[16]失去至亲如死亡或离婚，长时间工作和睡眠剥夺的状况下酪氨酸可以发挥作用，^[17]^[18]可以减少压力激素的程度，^[19]在动物试验中可以看出经由压力诱导的体重下降反应来减少这些情况，^[16]改善认知与物理性功能，^[14]^[20]^[21]在人类试验中，因为酪氨酸水解酶为速度限制酶，影响较左旋多巴胺不明显。

酪氨酸在正常情况下对情绪，认知或物理性功能并无明显影响，^[22]^[23]^[24] 在临床试验中每日成人剂量大约是100 毫克/公斤，相当于约6.8 克，^[25]通常剂量约为每天500-1500 毫克（大多数制造商建议剂量通常是相当于1-3粒纯酪氨酸），不建议超过每天12000 毫克（12克）。

白化症
黑尿症
Betalain
碘化酪氨酸衍生物
酪胺
酪氨酸硫酸化（英语：Tyrosine sulfation）
Tyrosinemia
Pauly reaction

[1]
IUPAC-IUBMB Joint Commission on Biochemical Nomenclature. Nomenclature and Symbolism for Amino Acids and Peptides. Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology. 1983 [2007-05-17]. （原始内容存档于2017-09-19）.
[2]
Tyrosine. The Columbia Electronic Encyclopedia, 6th ed. Infoplease.com — Columbia University Press. 2007 [2008-04-20]. （原始内容存档于2012-10-08）.
[3]
Douglas Harper. Tyrosine. Online Etymology Dictionary. 2001 [2008-04-20]. （原始内容存档于2016-11-08）.
[4]
Tyrosine. University of Maryland Medical Center. [2011-03-17]. （原始内容存档于2020-04-06）.
[5]
Hoffhines AJ, Damoc E, Bridges KG, Leary JA, Moore KL. Detection and purification of tyrosine-sulfated proteins using a novel anti-sulfotyrosine monoclonal antibody. J. Biol. Chem. 2006, 281 (49): 37877–87. PMC 1764208 . PMID 17046811. doi:10.1074/jbc.M609398200.
[6]
生物化学.上册第三版. 北京: 高等教育. 2002. ISBN 9787040110883.
[7]
Erowid Cacti Vault : Cactus Growers Guide. Erowid.org. 2008-03-08 [2013-04-16]. （原始内容存档于2021-05-19）.
[8]
Urinary phenolic acid metabolities of tyrosine. Booth A N, Masri M S, Robbins D J, Emerson O H, Jones F T and Deeds F, Journal of Biological Chemistry, 1960, Vol. 235, pages 2649-2652 (article （页面存档备份，存于互联网档案馆）)
[9]
Molnár GA, Wagner Z, Markó L, Kó Szegi T, Mohás M, Kocsis B, Matus Z, Wagner L, Tamaskó M, Mazák I, Laczy B, Nagy J, Wittmann I. Urinary ortho-tyrosine excretion in diabetes mellitus and renal failure: evidence for hydroxyl radical production. Kidney Int. 2005, 68 (5): 2281–7. PMID 16221230. doi:10.1111/j.1523-1755.2005.00687.x.
[10]
Molnár GA, Nemes V, Biró Z, Ludány A, Wagner Z, Wittmann I. Accumulation of the hydroxyl free radical markers meta-, ortho-tyrosine and DOPA in cataractous lenses is accompanied by a lower protein and phenylalanine content of the water-soluble phase. Free Radic. Res. 2005, 39 (12): 1359–66. PMID 16298866. doi:10.1080/10715760500307107.
[11]
Optimized Synthesis of L-m-Tyrosine Suitable for Chemical Scale-Up Cara E. Humphrey, Markus Furegati, Kurt Laumen, Luigi La Vecchia, Thomas Leutert, J. Constanze D. Müller-Hartwieg, and Markus Vögtle Organic Process Research & Development 2007, 11, 1069–1075 doi:10.1021/op700093y
[12]
Rasmussen DD, Ishizuka B, Quigley ME, Yen SS. Effects of tyrosine and tryptophan ingestion on plasma catecholamine and 3,4-dihydroxyphenylacetic acid concentrations. J. Clin. Endocrinol. Metab. 1983, 57 (4): 760–3. PMID 6885965. doi:10.1210/jcem-57-4-760.
[13]
Leathwood PD, Pollet P. Diet-induced mood changes in normal populations. Journal of Psychiatric Research. 1982, 17 (2): 147–54. PMID 6764931. doi:10.1016/0022-3956(82)90016-4.
[14]
Deijen JB, Orlebeke JF. Effect of tyrosine on cognitive function and blood pressure under stress. Brain Res. Bull. 1994, 33 (3): 319–23. PMID 8293316. doi:10.1016/0361-9230(94)90200-3.
[15]
Lieberman HR, Corkin S, Spring BJ, Wurtman RJ, Growdon JH. The effects of dietary neurotransmitter precursors on human behavior. Am J Clin Nutr. 1985, 42 (2): 366–370. PMID 4025206.
[16]
Hao S, Avraham Y, Bonne O, Berry EM. Separation-induced body weight loss, impairment in alternation behavior, and autonomic tone: effects of tyrosine. Pharmacol. Biochem. Behav. 2001, 68 (2): 273–81. PMID 11267632. doi:10.1016/S0091-3057(00)00448-2.
[17]
Magill RA, Waters WF, Bray GA, Volaufova J, Smith SR, Lieberman HR, McNevin N, Ryan DH. Effects of tyrosine, phentermine, caffeine D-amphetamine, and placebo on cognitive and motor performance deficits during sleep deprivation. Nutritional Neuroscience. 2003, 6 (4): 237–46. PMID 12887140. doi:10.1080/1028415031000120552.
[18]
Neri DF, Wiegmann D, Stanny RR, Shappell SA, McCardie A, McKay DL. The effects of tyrosine on cognitive performance during extended wakefulness. Aviation, space, and environmental medicine. 1995, 66 (4): 313–9. PMID 7794222.
[19]
Reinstein DK, Lehnert H, Wurtman RJ. Dietary tyrosine suppresses the rise in plasma corticosterone following acute stress in rats. Life Sci. 1985, 37 (23): 2157–63. PMID 4068899. doi:10.1016/0024-3205(85)90566-1.
[20]
Deijen JB, Wientjes CJ, Vullinghs HF, Cloin PA, Langefeld JJ. Tyrosine improves cognitive performance and reduces blood pressure in cadets after one week of a combat training course. Brain Res. Bull. 1999, 48 (2): 203–9. PMID 10230711. doi:10.1016/S0361-9230(98)00163-4.
[21]
Mahoney CR, Castellani J, Kramer FM, Young A, Lieberman HR. Tyrosine supplementation mitigates working memory decrements during cold exposure. Physiology and Behavior. 2007,. IN PRESS (4): 575–82. PMID 17585971. doi:10.1016/j.physbeh.2007.05.003.
[22]
Chinevere TD, Sawyer RD, Creer AR, Conlee RK, Parcell AC. Effects of L-tyrosine and carbohydrate ingestion on endurance exercise performance. J. Appl. Physiol. 2002, 93 (5): 1590–7. PMID 12381742. doi:10.1152/japplphysiol.00625.2001.
[23]
Strüder HK, Hollmann W, Platen P, Donike M, Gotzmann A, Weber K. Influence of paroxetine, branched-chain amino acids and tyrosine on neuroendocrine system responses and fatigue in humans. Horm. Metab. Res. 1998, 30 (4): 188–94. PMID 9623632. doi:10.1055/s-2007-978864.
[24]
Thomas JR, Lockwood PA, Singh A, Deuster PA. Tyrosine improves working memory in a multitasking environment. Pharmacol. Biochem. Behav. 1999, 64 (3): 495–500. PMID 10548261. doi:10.1016/S0091-3057(99)00094-5.
[25]
Gelenberg, A.J., Wojcik, J.D., Growdon, J.H., Sved, A.F., and Wurtman, R.J. Tyrosine for the Treatment of Depression (PDF). [2008-03-25]. （原始内容 (PDF)存档于2008-06-11）.

Tyrosine MS Spectrum （页面存档备份，存于互联网档案馆）
Tyrosine metabolism （页面存档备份，存于互联网档案馆）
Phenylalanine and tyrosine biosynthesis （页面存档备份，存于互联网档案馆）
Phenylalanine, Tyrosine, and tryptophan biosynthesis （页面存档备份，存于互联网档案馆）

Template:Psychostimulants, agents used for ADHD and nootropics（英语：Template:Psychostimulants, agents used for ADHD and nootropics） Template:Dopaminergics（英语：Template:Dopaminergics）

[1] [1]
IUPAC-IUBMB Joint Commission on Biochemical Nomenclature. Nomenclature and Symbolism for Amino Acids and Peptides. Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology. 1983 [2007-05-17]. （原始内容存档于2017-09-19）.

[urltyrosine_—_Infoplease.com-2] [2]
Tyrosine. The Columbia Electronic Encyclopedia, 6th ed. Infoplease.com — Columbia University Press. 2007 [2008-04-20]. （原始内容存档于2012-10-08）.

[urlOnline_Etymology_Dictionary-3] [3]
Douglas Harper. Tyrosine. Online Etymology Dictionary. 2001 [2008-04-20]. （原始内容存档于2016-11-08）.

[4] [4]
Tyrosine. University of Maryland Medical Center. [2011-03-17]. （原始内容存档于2020-04-06）.

[pmid17046811-5] [5]
Hoffhines AJ, Damoc E, Bridges KG, Leary JA, Moore KL. Detection and purification of tyrosine-sulfated proteins using a novel anti-sulfotyrosine monoclonal antibody. J. Biol. Chem. 2006, 281 (49): 37877–87. PMC 1764208 . PMID 17046811. doi:10.1074/jbc.M609398200.

[:0-6] [6]
生物化学.上册第三版. 北京: 高等教育. 2002. ISBN 9787040110883.

[7] [7]
Erowid Cacti Vault : Cactus Growers Guide. Erowid.org. 2008-03-08 [2013-04-16]. （原始内容存档于2021-05-19）.

[8] [8]
Urinary phenolic acid metabolities of tyrosine. Booth A N, Masri M S, Robbins D J, Emerson O H, Jones F T and Deeds F, Journal of Biological Chemistry, 1960, Vol. 235, pages 2649-2652 (article （页面存档备份，存于互联网档案馆）)

[pmid16221230-9] [9]
Molnár GA, Wagner Z, Markó L, Kó Szegi T, Mohás M, Kocsis B, Matus Z, Wagner L, Tamaskó M, Mazák I, Laczy B, Nagy J, Wittmann I. Urinary ortho-tyrosine excretion in diabetes mellitus and renal failure: evidence for hydroxyl radical production. Kidney Int. 2005, 68 (5): 2281–7. PMID 16221230. doi:10.1111/j.1523-1755.2005.00687.x.

[pmid16298866-10] [10]
Molnár GA, Nemes V, Biró Z, Ludány A, Wagner Z, Wittmann I. Accumulation of the hydroxyl free radical markers meta-, ortho-tyrosine and DOPA in cataractous lenses is accompanied by a lower protein and phenylalanine content of the water-soluble phase. Free Radic. Res. 2005, 39 (12): 1359–66. PMID 16298866. doi:10.1080/10715760500307107.

[11] [11]
Optimized Synthesis of L-m-Tyrosine Suitable for Chemical Scale-Up Cara E. Humphrey, Markus Furegati, Kurt Laumen, Luigi La Vecchia, Thomas Leutert, J. Constanze D. Müller-Hartwieg, and Markus Vögtle Organic Process Research & Development 2007, 11, 1069–1075 doi:10.1021/op700093y

[pmid6885965-12] [12]
Rasmussen DD, Ishizuka B, Quigley ME, Yen SS. Effects of tyrosine and tryptophan ingestion on plasma catecholamine and 3,4-dihydroxyphenylacetic acid concentrations. J. Clin. Endocrinol. Metab. 1983, 57 (4): 760–3. PMID 6885965. doi:10.1210/jcem-57-4-760.

[DietMood-13] [13]
Leathwood PD, Pollet P. Diet-induced mood changes in normal populations. Journal of Psychiatric Research. 1982, 17 (2): 147–54. PMID 6764931. doi:10.1016/0022-3956(82)90016-4.

[CognBPStress-14] [14]
Deijen JB, Orlebeke JF. Effect of tyrosine on cognitive function and blood pressure under stress. Brain Res. Bull. 1994, 33 (3): 319–23. PMID 8293316. doi:10.1016/0361-9230(94)90200-3.

[DietNeur-15] [15]
Lieberman HR, Corkin S, Spring BJ, Wurtman RJ, Growdon JH. The effects of dietary neurotransmitter precursors on human behavior. Am J Clin Nutr. 1985, 42 (2): 366–370. PMID 4025206.

[pmid11267632-16] [16]
Hao S, Avraham Y, Bonne O, Berry EM. Separation-induced body weight loss, impairment in alternation behavior, and autonomic tone: effects of tyrosine. Pharmacol. Biochem. Behav. 2001, 68 (2): 273–81. PMID 11267632. doi:10.1016/S0091-3057(00)00448-2.

[pmid12887140-17] [17]
Magill RA, Waters WF, Bray GA, Volaufova J, Smith SR, Lieberman HR, McNevin N, Ryan DH. Effects of tyrosine, phentermine, caffeine D-amphetamine, and placebo on cognitive and motor performance deficits during sleep deprivation. Nutritional Neuroscience. 2003, 6 (4): 237–46. PMID 12887140. doi:10.1080/1028415031000120552.

[pmid7794222-18] [18]
Neri DF, Wiegmann D, Stanny RR, Shappell SA, McCardie A, McKay DL. The effects of tyrosine on cognitive performance during extended wakefulness. Aviation, space, and environmental medicine. 1995, 66 (4): 313–9. PMID 7794222.

[pmid4068899-19] [19]
Reinstein DK, Lehnert H, Wurtman RJ. Dietary tyrosine suppresses the rise in plasma corticosterone following acute stress in rats. Life Sci. 1985, 37 (23): 2157–63. PMID 4068899. doi:10.1016/0024-3205(85)90566-1.

[Cadets-20] [20]
Deijen JB, Wientjes CJ, Vullinghs HF, Cloin PA, Langefeld JJ. Tyrosine improves cognitive performance and reduces blood pressure in cadets after one week of a combat training course. Brain Res. Bull. 1999, 48 (2): 203–9. PMID 10230711. doi:10.1016/S0361-9230(98)00163-4.

[MemoryCold-21] [21]
Mahoney CR, Castellani J, Kramer FM, Young A, Lieberman HR. Tyrosine supplementation mitigates working memory decrements during cold exposure. Physiology and Behavior. 2007,. IN PRESS (4): 575–82. PMID 17585971. doi:10.1016/j.physbeh.2007.05.003.

[pmid12381742-22] [22]
Chinevere TD, Sawyer RD, Creer AR, Conlee RK, Parcell AC. Effects of L-tyrosine and carbohydrate ingestion on endurance exercise performance. J. Appl. Physiol. 2002, 93 (5): 1590–7. PMID 12381742. doi:10.1152/japplphysiol.00625.2001.

[pmid9623632-23] [23]
Strüder HK, Hollmann W, Platen P, Donike M, Gotzmann A, Weber K. Influence of paroxetine, branched-chain amino acids and tyrosine on neuroendocrine system responses and fatigue in humans. Horm. Metab. Res. 1998, 30 (4): 188–94. PMID 9623632. doi:10.1055/s-2007-978864.

[pmid10548261-24] [24]
Thomas JR, Lockwood PA, Singh A, Deuster PA. Tyrosine improves working memory in a multitasking environment. Pharmacol. Biochem. Behav. 1999, 64 (3): 495–500. PMID 10548261. doi:10.1016/S0091-3057(99)00094-5.

[25] [25]
Gelenberg, A.J., Wojcik, J.D., Growdon, J.H., Sved, A.F., and Wurtman, R.J. Tyrosine for the Treatment of Depression (PDF). [2008-03-25]. （原始内容 (PDF)存档于2008-06-11）.

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