碲半胱氨酸

碲半胱氨酸
	IUPAC名; (2R)-2-Amino-3-tellanylpropanoic acid
别名	碲代半胱氨酸
识别
CAS号	122096-31-5
PubChem	129631934
ChemSpider	34500822
SMILES	C(C(C(=O)O)N)[TeH];
性质
化学式	C3H7NO2Te
摩尔质量	216.69 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

碲半胱氨酸，又称Te-Cys是一种结构类似丝氨酸、半胱氨酸和硒半胱氨酸的氨基酸，由碲原子取代侧链的氧、硫或硒而成。它不存在于生物体中。

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性质

也许是因为碳-碲键键能低（200 kJ/mol，相较于碳-硒键键能234 kJ/mol和碳-硫键键能272 kJ/mol），^[1]碲半胱氨酸不存在于任何已知的天然生物体中，因此它的研究相比硒代半胱氨酸相对不足。^[2]尽管如此，某些生物如真菌烟曲霉在无硫环境中，能够将碲半胱氨酸和碲甲硫氨酸结合到氨基酸和蛋白质中。^[3]

已经观察到，当掺入谷胱甘肽S-转移酶时，碲半胱氨酸能有效地抑制氨酰化（英语：Aminoacylation），并增加谷胱甘肽过氧化物酶的效率。^[4]

制备

L-碲半胱氨酸可以由碲单质和(2R)-2-[(叔丁氧基羰基)氨基]-3-碘丙酸甲酯在四氢呋喃溶液在三乙基硼氢化锂下反应而成，会产生红色油状物。之后酸化并用碱处理，然后用柠檬酸处理，将pH值设为4.0，过滤和干燥后得到橙色固体（碲半胱氨酸）。^[5]

参考资料

[1]
Chivers, Tristram; Laitinen, Risto S. Tellurium: a maverick among the chalcogens. Chemical Society Reviews. 23 March 2015, 44 (7): 1725–1739. ISSN 1460-4744. PMID 25692398. doi:10.1039/C4CS00434E （英语）.
[2]
Advances in Microbial Physiology. Academic Press. 2007: 4 [2021-08-15]. ISBN 9780080560649. （原始内容存档于2021-08-27）（英语）.
[3]
Ramadan, ShadiaE.; Razak, A.A.; Ragab, A.M.; El-Meleigy, M. Incorporation of tellurium into amino acids and proteins in a tellurium-tolerant fungi. Biological Trace Element Research. 1 June 1989, 20 (3): 225–232. ISSN 0163-4984. PMID 2484755. S2CID 9439946. doi:10.1007/BF02917437 （英语）.
[4]
Liu, Xiaoman; Silks, Louis A.; Liu, Cuiping; Ollivault-Shiflett, Morgane; Huang, Xin; Li, Jing; Luo, Guimin; Hou, Ya-Ming; Liu, Junqiu; Shen, Jiacong. Incorporation of Tellurocysteine into Glutathione Transferase Generates High Glutathione Peroxidase Efficiency. Angewandte Chemie International Edition. 2 March 2009, 48 (11): 2020–2023. PMID 19199319. doi:10.1002/anie.200805365.
[5]
Stocking, Emily M.; Schwarz, Jessie N.; Senn, Hans; Salzmann, Michael; Silks, Louis A. Synthesis of L-selenocystine,L-[77Se]selenocystine and L-tellurocystine. Journal of the Chemical Society, Perkin Transactions 1. 1 January 1997, 0 (16): 2443–2448. ISSN 1364-5463. doi:10.1039/A600180G （英语）.

[1] [1]
Chivers, Tristram; Laitinen, Risto S. Tellurium: a maverick among the chalcogens. Chemical Society Reviews. 23 March 2015, 44 (7): 1725–1739. ISSN 1460-4744. PMID 25692398. doi:10.1039/C4CS00434E （英语）.

[2] [2]
Advances in Microbial Physiology. Academic Press. 2007: 4 [2021-08-15]. ISBN 9780080560649. （原始内容存档于2021-08-27）（英语）.

[3] [3]
Ramadan, ShadiaE.; Razak, A.A.; Ragab, A.M.; El-Meleigy, M. Incorporation of tellurium into amino acids and proteins in a tellurium-tolerant fungi. Biological Trace Element Research. 1 June 1989, 20 (3): 225–232. ISSN 0163-4984. PMID 2484755. S2CID 9439946. doi:10.1007/BF02917437 （英语）.

[4] [4]
Liu, Xiaoman; Silks, Louis A.; Liu, Cuiping; Ollivault-Shiflett, Morgane; Huang, Xin; Li, Jing; Luo, Guimin; Hou, Ya-Ming; Liu, Junqiu; Shen, Jiacong. Incorporation of Tellurocysteine into Glutathione Transferase Generates High Glutathione Peroxidase Efficiency. Angewandte Chemie International Edition. 2 March 2009, 48 (11): 2020–2023. PMID 19199319. doi:10.1002/anie.200805365.

[5] [5]
Stocking, Emily M.; Schwarz, Jessie N.; Senn, Hans; Salzmann, Michael; Silks, Louis A. Synthesis of L-selenocystine,L-[77Se]selenocystine and L-tellurocystine. Journal of the Chemical Society, Perkin Transactions 1. 1 January 1997, 0 (16): 2443–2448. ISSN 1364-5463. doi:10.1039/A600180G （英语）.

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