羊毛硫氨酸

羊毛硫氨酸
	IUPAC名; S-[(2R)-2-Amino-2-carboxyethyl]-L-cysteine
識別
CAS號	922-55-4
PubChem	256406
ChemSpider	88959
SMILES	O=C(O)[C@@H](N)CSC[C@H](N)C(=O)O;
InChI	1/C6H12N2O4S/c7-3(5(9)10)1-13-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1;
InChIKey	DWPCPZJAHOETAG-IMJSIDKUBX
ChEBI	21347
性質
化學式	C6H12N2O4S
摩爾質量	208.2318 g·mol⁻¹
熔點	280 - 283 °C（270 K）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

羊毛硫氨酸（英語：Lanthionine，縮寫LAN）是一種非蛋白質氨基酸，化學式為 C₆H₁₂N₂O₄S。其在生物體內常由半胱氨酸殘基與脫水絲氨酸殘基結合得到。

歷史

羊毛硫氨酸於1941年首次從碳酸鈉處理過的羊毛中分離得到，並發現其為一種含硫氨基酸，於是根據羊毛拉丁語「Lana」和硫希臘語「theîon」命名為「lanthionine」^[1]。羊毛硫氨酸的首次人工製備是利用3-氯丙氨酸與半胱氨酸發生烷基化反應實現^[2]。

分佈

羊毛硫氨酸在自然界中廣泛存在，人們已在毛髮、乳白蛋白以及羽毛中得到了羊毛硫氨酸。在細菌細胞壁以及一些微生物基因編碼產生的肽類抗生素中也發現了羊毛硫氨酸。這類抗生素被稱為羊毛硫抗生素（lantibiotics），如食品防腐劑乳酸鏈球菌素^[3]、枯草菌素、表皮素（用於殺滅葡萄球菌和鏈球菌）、阿肽加定、以及血管緊張肽轉化酶抑制肽（ancovenin）等^[4]^[5]。

製備

現已報道了多種羊毛硫氨酸合成方法，如絲氨酸硫化法^[6]、絲氨酸β-內酯開環法^[5]、脫氫丙氨酸與絲氨酸雜共軛加成法等^[7]。然而在羊毛硫抗生素的全合成中，只採納了第一種方法。

生物合成含有羊毛硫氨酸橋接的肽類產物有多種途徑，例如，乳酸鏈球菌合成乳酸鏈球菌素中的羊毛硫氨酸的過程中，用到了專門的脫水酶 (NisB) 和環化酶 (NisC)^[8]^[9]。

參考文獻

^ Horn, M. J.; Jones, D. B.; Ringel, S. J. (1941) Isolation of a New Sulfur-Containing Amino Acid (Lanthionine) from Sodium Carbonate-Treated Wool. Journal of Biological Chemistry, 138, 141-149.
^ Brown, G. B.; du Vigneaud, V. (1941) The Stereoisomeric Forms of Lanthionine. Journal of Biological Chemistry, 140, 767-771.
^ 中國食品添加劑生產應用工業協會 (編). (十六) 乳酸链球菌素 Nisin. 食品添加剂手册. 北京: 中國輕工業出版社. 1996.
^ Paul, M.; van der Donk, W. A. (2005) Chemical and Enzymatic Synthesis of Lanthionines. Mini-Reviews in Organic Chemistry, 2, 23-37.
^ ^5.0 ^5.1 Shao, H.; Wang, S. H. H.; Lee, C.-W.; Ösapay, G.; Goodman, M. (1995) A Facile Synthesis of Orthogonally Protected Stereoisomeric Lanthionines by Regioselective Ring Opening of Serine β-Lactone Derivatives. Journal of Organic Chemistry, 60, 2956-2957.
^ Harpp, D. N.; Gleason, J. G. (1971) Preparation and Mass Spectral Properties of Cystine and Lanthionine Derivatives. Novel Synthesis of L-Lanthionine by Selective Desulfurization. Journal of Organic Chemistry, 36, 73-80.
^ Probert, J. M.; Rennex, D.; Bradley, M. (1996) Lanthionines for Solid Phase Synthesis. Tetrahedron Letters, 37, 1101-1104.
^ Arnison PG, Bibb MJ, Bierbaum G, Bowers AA, Bugni TS, Bulaj G, Camarero JA, Campopiano DJ, Challis GL, Clardy J, Cotter PD, Craik DJ, Dawson M, Dittmann E, Donadio S, Dorrestein PC, Entian KD, Fischbach MA, Garavelli JS, Göransson U, Gruber CW, Haft DH, Hemscheidt TK, Hertweck C, Hill C, Horswill AR, Jaspars M, Kelly WL, Klinman JP, Kuipers OP, Link AJ, Liu W, Marahiel MA, Mitchell DA, Moll GN, Moore BS, Müller R, Nair SK, Nes IF, Norris GE, Olivera BM, Onaka H, Patchett ML, Piel J, Reaney MJ, Rebuffat S, Ross RP, Sahl HG, Schmidt EW, Selsted ME, Severinov K, Shen B, Sivonen K, Smith L, Stein T, Süssmuth RD, Tagg JR, Tang GL, Truman AW, Vederas JC, Walsh CT, Walton JD, Wenzel SC, Willey JM, van der Donk WA. Ribosomally synthesized and post-translationally modified peptide natural products: overview and recommendations for a universal nomenclature. Nat Prod Rep. 2013, 30 (1): 108–60. PMC 3954855  . PMID 23165928. doi:10.1039/c2np20085f.
^ Knerr PJ, van der Donk WA. Discovery, biosynthesis, and engineering of lantipeptides. Annu. Rev. Biochem. 2012, 81: 479–505. PMID 22404629. doi:10.1146/annurev-biochem-060110-113521.

[1] Horn, M. J.; Jones, D. B.; Ringel, S. J. (1941) Isolation of a New Sulfur-Containing Amino Acid (Lanthionine) from Sodium Carbonate-Treated Wool. Journal of Biological Chemistry, 138, 141-149.

[2] Brown, G. B.; du Vigneaud, V. (1941) The Stereoisomeric Forms of Lanthionine. Journal of Biological Chemistry, 140, 767-771.

[3] 中國食品添加劑生產應用工業協會 (編). (十六) 乳酸链球菌素 Nisin. 食品添加剂手册. 北京: 中國輕工業出版社. 1996.

[4] Paul, M.; van der Donk, W. A. (2005) Chemical and Enzymatic Synthesis of Lanthionines. Mini-Reviews in Organic Chemistry, 2, 23-37.

[shao-5] 5.0 ^5.1 Shao, H.; Wang, S. H. H.; Lee, C.-W.; Ösapay, G.; Goodman, M. (1995) A Facile Synthesis of Orthogonally Protected Stereoisomeric Lanthionines by Regioselective Ring Opening of Serine β-Lactone Derivatives. Journal of Organic Chemistry, 60, 2956-2957.

[6] Harpp, D. N.; Gleason, J. G. (1971) Preparation and Mass Spectral Properties of Cystine and Lanthionine Derivatives. Novel Synthesis of L-Lanthionine by Selective Desulfurization. Journal of Organic Chemistry, 36, 73-80.

[7] Probert, J. M.; Rennex, D.; Bradley, M. (1996) Lanthionines for Solid Phase Synthesis. Tetrahedron Letters, 37, 1101-1104.

[8] Arnison PG, Bibb MJ, Bierbaum G, Bowers AA, Bugni TS, Bulaj G, Camarero JA, Campopiano DJ, Challis GL, Clardy J, Cotter PD, Craik DJ, Dawson M, Dittmann E, Donadio S, Dorrestein PC, Entian KD, Fischbach MA, Garavelli JS, Göransson U, Gruber CW, Haft DH, Hemscheidt TK, Hertweck C, Hill C, Horswill AR, Jaspars M, Kelly WL, Klinman JP, Kuipers OP, Link AJ, Liu W, Marahiel MA, Mitchell DA, Moll GN, Moore BS, Müller R, Nair SK, Nes IF, Norris GE, Olivera BM, Onaka H, Patchett ML, Piel J, Reaney MJ, Rebuffat S, Ross RP, Sahl HG, Schmidt EW, Selsted ME, Severinov K, Shen B, Sivonen K, Smith L, Stein T, Süssmuth RD, Tagg JR, Tang GL, Truman AW, Vederas JC, Walsh CT, Walton JD, Wenzel SC, Willey JM, van der Donk WA. Ribosomally synthesized and post-translationally modified peptide natural products: overview and recommendations for a universal nomenclature. Nat Prod Rep. 2013, 30 (1): 108–60. PMC 3954855  . PMID 23165928. doi:10.1039/c2np20085f.

[9] Knerr PJ, van der Donk WA. Discovery, biosynthesis, and engineering of lantipeptides. Annu. Rev. Biochem. 2012, 81: 479–505. PMID 22404629. doi:10.1146/annurev-biochem-060110-113521.

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羊毛硫氨酸

IUPAC名 S-[(2R)-2-Amino-2-carboxyethyl]-L-cysteine
識別
CAS號	922-55-4 ^Y
PubChem	256406
ChemSpider	88959
SMILES	O=C(O)[C@@H](N)CSC[C@H](N)C(=O)O
InChI	1/C6H12N2O4S/c7-3(5(9)10)1-13-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1
InChIKey	DWPCPZJAHOETAG-IMJSIDKUBX
ChEBI	21347
性質
化學式	C₆H₁₂N₂O₄S
摩爾質量	208.2318 g·mol⁻¹
熔點	280 - 283 °C（270 K）
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。