N(tau)-甲基-l-组氨酸盐酸盐 | 200926-96-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N(tau)-甲基-l-组氨酸盐酸盐
• 英文名称: (S)-1-carboxy-2-(1-methyl-1H-imidazol-4-yl)ethanaminium chloride
• 英文别名: N(π)-methyl-L-histidine hydrochloride；1-methyl-L-histidine ; hydrochloride；1-Methyl-L-histidin; Hydrochlorid；(s)-1-Carboxy-2-(1-methyl-1h-imidazol-4-yl) ethanaminium chloride；[(1S)-1-carboxy-2-(1-methylimidazol-4-yl)ethyl]azanium;chloride
• CAS: 200926-96-1
• 化学式: C₇H₁₁N₃O₂*ClH
• 分子量: 205.644
• InChiKey: UYSVQTDJUMYKHZ-RGMNGODLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  81.1
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  N(tau)-甲基-l-组氨酸盐酸盐 在 N-甲基吗啉 、 盐酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 (S)-methyl 2-(3-(t-butoxycarbonylamino)propanamido)-3-(1-methyl-1H-imidazol-4-yl)propanoate
  参考文献：
  名称：

  Carnosine protects cardiac myocytes against lipid peroxidation products

  摘要：

  Endogenous histidyl dipeptides such as carnosine (-alanine-l-histidine) form conjugates with lipid peroxidation products such as 4-hydroxy-trans-2-nonenal (HNE and acrolein), chelate metals, and protect against myocardial ischemic injury. Nevertheless, it is unclear whether these peptides protect against cardiac injury by directly reacting with lipid peroxidation products. Hence, to examine whether changes in the structure of carnosine could affect its aldehyde reactivity and metal chelating ability, we synthesized methylated analogs of carnosine, balenine (-alanine-N-methylhistidine) and dimethyl balenine (DMB), and measured their aldehyde reactivity and metal chelating properties. We found that methylation of N residue of imidazole ring (balenine) or trimethylation of carnosine backbone at N residue of imidazole ring and terminal amine group dimethyl balenine (DMB) abolishes the ability of these peptides to react with HNE. Incubation of balenine with acrolein resulted in the formation of single product (m/z 297), whereas DMB did not react with acrolein. In comparison with carnosine, balenine exhibited moderate acrolein quenching capacity. The Fe2+ chelating ability of balenine was higher than that of carnosine, whereas DMB lacked chelating capacity. Pretreatment of cardiac myocytes with carnosine increased the mean lifetime of myocytes superfused with HNE or acrolein compared with balenine or DMB. Collectively, these results suggest that carnosine protects cardiac myocytes against HNE and acrolein toxicity by directly reacting with these aldehydes. This reaction involves both the amino group of -alanyl residue and the imidazole residue of l-histidine. Methylation of these sites prevents or abolishes the aldehyde reactivity of carnosine, alters its metal-chelating property, and diminishes its ability to prevent electrophilic injury.

  DOI：

  10.1007/s00726-018-2676-6
• 作为产物：
  描述：

  S-(+)-7-Methoxycarbonyl-5,6,7,8-tetrahydroimidazo<1,5-c>pyrimidin-5-on 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 22.0h， 生成 N(tau)-甲基-l-组氨酸盐酸盐
  参考文献：
  名称：

  Carnosine protects cardiac myocytes against lipid peroxidation products

  摘要：

  Endogenous histidyl dipeptides such as carnosine (-alanine-l-histidine) form conjugates with lipid peroxidation products such as 4-hydroxy-trans-2-nonenal (HNE and acrolein), chelate metals, and protect against myocardial ischemic injury. Nevertheless, it is unclear whether these peptides protect against cardiac injury by directly reacting with lipid peroxidation products. Hence, to examine whether changes in the structure of carnosine could affect its aldehyde reactivity and metal chelating ability, we synthesized methylated analogs of carnosine, balenine (-alanine-N-methylhistidine) and dimethyl balenine (DMB), and measured their aldehyde reactivity and metal chelating properties. We found that methylation of N residue of imidazole ring (balenine) or trimethylation of carnosine backbone at N residue of imidazole ring and terminal amine group dimethyl balenine (DMB) abolishes the ability of these peptides to react with HNE. Incubation of balenine with acrolein resulted in the formation of single product (m/z 297), whereas DMB did not react with acrolein. In comparison with carnosine, balenine exhibited moderate acrolein quenching capacity. The Fe2+ chelating ability of balenine was higher than that of carnosine, whereas DMB lacked chelating capacity. Pretreatment of cardiac myocytes with carnosine increased the mean lifetime of myocytes superfused with HNE or acrolein compared with balenine or DMB. Collectively, these results suggest that carnosine protects cardiac myocytes against HNE and acrolein toxicity by directly reacting with these aldehydes. This reaction involves both the amino group of -alanyl residue and the imidazole residue of l-histidine. Methylation of these sites prevents or abolishes the aldehyde reactivity of carnosine, alters its metal-chelating property, and diminishes its ability to prevent electrophilic injury.

  DOI：

  10.1007/s00726-018-2676-6

文献信息

• 一种鲸肌肽及其中间体的制备方法
  申请人：南京纽邦生物科技有限公司

  公开号：CN109748875A

  公开（公告）日：2019-05-14

  本发明提供了两种鲸肌肽的制备方法，以及一种合成鲸肌肽中间体的制备方法，操作简单易行、工艺稳定、易于控制、反应后处理方便、产物收率好，纯度高，可以经济方便地用于工业化生产。
• The Pictet-Spengler Reaction on L-Histidine. Preparation of Conformationally Restricted (+)-Pilocarpine Analogs.
  作者：M. del Mar Sánchez-Sánchez、L. M. Tel-Alberdi、M. Jesus Rioseras、M. del Rosario Rico-Ferreira、F. Bermejo-González

  DOI：10.1246/bcsj.66.191

  日期：——

  The total regioselective synthesis of the rigid (+)-pilocarpine analogs 4—6 starting from L-histidine is described. The Pictet-Spengler condensation is used to prepare the tetrahydroimidazopyridine moiety present in the structure of these tricyclic derivatives.

  描述了从 L-组氨酸开始的刚性 (+)-毛果芸香碱类似物 4-6 的总区域选择性合成。Pictet-Spengler 缩合用于制备存在于这些三环衍生物结构中的四氢咪唑并吡啶部分。
• Mimicking of the histidine brace structural motif in molecular copper(I) compounds
  作者：R. Peifer、L. Müller、S. Hoof、F. Beckmann、B. Cula、C. Limberg

  DOI：10.1002/zaac.202100145

  日期：2021.9.27

  Bpm=di(3-(phenyl)-1H-pyrazol-1-yl)diphenylmethane, di(3-(mesityl)-1H-pyrazol-1-yl)methane and di(3-(tert-butyl)-1H-pyrazol-1-yl)diphenylmethane). Addition of MeHisOMe to these complexes led to products that were so sensitive towards oxidation by the environment that they eluded isolation. One experiment provided blue crystals as a product of such a reaction. They belonged to a salt with a complex cation

  L-Nτ-甲基组氨酸甲酯，MeHisOMe，已被用作一种潜在的配体，以模拟酶（如微粒甲烷单加氧酶或裂解多糖单加氧酶）中铜离子的组氨酸支架型配位。MeHisOMe 是通过组氨酸甲酯的双甲基化制备的。随后，测试了其与二膦铜 (I) 前体 [Cu(P^P)(MeCN) 2 ]BF 4的络合，这导致了络合物 [Cu(P^P)(MeHisOMe)]BF 4 (P^P =dpePhos: 1 , P^P=XantPhos: 2 , P^P=dppf: 3 )。1 – 3也通过单晶 X 射线分析进行了充分表征，从而为铜配合物与合成的、真实的组氨酸支架提供了第一个结构数据。该配合物在与分子氧接触时被证明是惰性的。为了改善仿生特性，尝试用双（吡唑基）甲烷，Bpm 正式取代二膦配体。相应地，合成了[BpmCu(NCMe) x ]BF 4前驱体，在吡唑基的3-位具有不同的取代基（即Bpm=二（3-（苯基）-1H-吡唑-1-基）二苯基甲烷，二（