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组氨酸甲酯

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组氨酸甲酯
别名 Methyl L-histidinate, HME
识别
CAS号 1499-46-3  checkY
7389-87-9(HCl)  ☒N
PubChem 92893
ChemSpider 83857
SMILES
 
  • COC(=O)[C@H](Cc1c[nH]cn1)N
Beilstein 957974
EINECS 216-109-3
ChEBI 70961
性质
化学式 C7H11N3O2
摩尔质量 169.18 g·mol−1
熔点 62-66 °C[1]
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

组氨酸甲酯(英語:Histidine methyl ester,缩写HME)是一种氨基酸酯,化学式为C7H11N3O2,可作为组氨酸脱羧酶的不可逆抑制剂[2][3][4]。它和苯甲醛反应,经氰基硼氢化钠还原, 可以得到N-苄基组氨酸甲酯[5]

组氨酸甲酯与组氨酸脱羧酶结合

参考文献

  1. ^ Merrifield, R. B.; Woolley, D. W. The Synthesis of L-Seryl-L-histidyl-L-leucyl-L-valyl- L-glutamic Acid, a Peptide with Strepogenin Activity. Journal of the American Chemical Society. 1956-09, 78 (18): 4646–4649. doi:10.1021/ja01599a032. 
  2. ^ Lane, Roger S; Manning, James M; Snell, Esmond E. Histidine decarboxylase of lactobacillus 30a: inactivation and active-site labeling by L-histidine methyl ester. Biochemistry. 2002, 15 (19): 4180–5. PMID 963031. doi:10.1021/bi00664a008. 
  3. ^ Alston, Theodore A; Abeles, Robert H. Reaction of Lactobacillus histidine decarboxylase with L-histidine methyl ester. Biochemistry. 2002, 26 (13): 4082–5. PMID 3651438. doi:10.1021/bi00387a051. 
  4. ^ Komori, H; Nitta, Y; Ueno, H; Higuchi, Y. Structural Study Reveals That Ser-354 Determines Substrate Specificity on Human Histidine Decarboxylase. The Journal of Biological Chemistry. 2012, 287 (34): 29175–83. PMC 3436558可免费查阅. PMID 22767596. doi:10.1074/jbc.M112.381897可免费查阅. 
  5. ^ Roy, Moumita Singha; Meng, Xiaofeng; Koda, Karuna; Shrestha, Andrina; Putman, Joshua I; Gout, Delphine; Armstrong, Daniel W.; Lovely, Carl J. Total synthesis of haploscleridamine, villagorgin A and an approach towards lissoclin C. Organic & Biomolecular Chemistry. 2023, 21 (7): 1422–1434. doi:10.1039/D2OB01908F.