methioninamide hydrochloride | 52811-68-4

• 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
• 英文名称: methioninamide hydrochloride
• 英文别名: methionine amide hydrochloride；(1-amino-4-methylsulfanyl-1-oxobutan-2-yl)azanium;chloride
• CAS: 52811-68-4
• 化学式: C₅H₁₂N₂OS*ClH
• 分子量: 184.69
• InChiKey: PWCBMJHINDTXGV-UHFFFAOYSA-N

物化性质

• 熔点：
  192 °C(Solv: acetone, 80% (67-64-1))

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  94.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methioninamide hydrochloride 在 Escherichia coli JM₁₀₉ 、 pCl₃₈DP 作用下， 以 various solvent(s) 为溶剂， 反应 10.0h， 以97%的产率得到D-蛋氨酸
  参考文献：
  名称：

  Asano, Yasuhisa; Kishino, Katsuhiko; Yamada, Akiko, Recueil des Travaux Chimiques des Pays-Bas, 1991, vol. 110, # 5, p. 206 - 208

  摘要：

  DOI：
• 作为产物：
  描述：

  DL-蛋氨酸 在 盐酸 、 氯甲酸乙酯 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 methioninamide hydrochloride
  参考文献：
  名称：

  The development of a new class of inhibitors for betaine-homocysteine S-methyltransferase

  摘要：

  Betaine-homocysteine S-methyltransferase (BHMT) is an important zinc-dependent methyltransferase that uses betaine as the methyl donor for the remethylation of homocysteine to form methionine. In the liver, BHMT performs to half of the homocysteine remethylation. In this study, we systematically investigated the tolerance of the enzyme for modifications at the "homocysteine" part of the previously reported potent inhibitor (R,S)-5-(3-amino-3-carboxy-propylsulfanyl)-pentanoic acid (1). In the new compounds, which are S-alkylated homocysteine derivatives, we replaced the carboxylic group in the "homocysteine" part of inhibitor 1 with different isosteric moieties (tetrazole and oxadiazolone); we suppressed the carboxylic negative charge by amidations; we enhanced acidity by replacing the carboxylate with phosphonic or phosphinic acids; and we introduced pyrrolidine steric constraints. Some of these compounds display high affinity toward human BHMT and may be useful for further pharmacological studies of this enzyme. Although none of the new compounds were more potent inhibitors than the reference inhibitor 1, this study helped to completely define the structural requirements of the active site of BHMT and revealed the remarkable selectivity of the enzyme for homocysteine. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.039

文献信息

• DIPEPTIDE MIMETICS OF NGF AND BDNF NEUROTROPHINS
  申请人：Seredenin Sergey Borisovich

  公开号：US20110312895A1

  公开（公告）日：2011-12-22

  The invention relates to compounds having either agonist or antagonist activities for the neurotrophins NGF and BDNF and represented by monomeric or dimeric substituted dipeptides that are analogs of the exposed portions of loop 1 or loop 4 regions of these neurotrophins near or at a beta-turn of the respective loop. N-acylated substituents of these dipeptides are biostereoisomers of the amino acid residues preceding these dipeptide sequences in the neurotrophin primary structure. The dimeric structure is produced advantageously by using hexamethylenediamine to which dipeptides are attached via their carboxyl groups. The claimed compounds displayed neuroprotective and differentiation-inducing activities in cellular models and enhanced the amount of phosphorylated tyrosine kinase A and the heat shock proteins Hsp32 and Hsp70 in the concentration range of 10 −9 to 10 −5 M. They also displayed neuroprotective, anti-parkinsonian, anti-stroke, anti-ischemic, anti-depressant and anti-amnestic activities in animal models and were active in experimental models of Alzheimer's disease. These in vivo effects of the claimed compounds are displayed in the dose range of 0.01 to 10 mg/kg when administered intraperitoneally.

  该发明涉及具有神经营养因子NGF和BDNF的激动剂或拮抗剂活性的化合物，这些化合物由单体或二聚体取代二肽代表，这些二肽代表这些神经营养因子的环1或环4区域的暴露部分的类似物，靠近或在各自环的β-转弯处。这些二肽的N-酰化取代物是神经营养因子原始结构中这些二肽序列之前的氨基酸残基的生物立体异构体。通过使用己二胺，优点地产生二聚体结构，二肽通过它们的羧基团连接到己二胺上。所述化合物在细胞模型中显示出神经保护和诱导分化活性，并在浓度范围为10^(-9)到10^(-5)M时增加了磷酸化酪氨酸激酶A和热休克蛋白Hsp32和Hsp70的量。它们还在动物模型中显示出神经保护、抗帕金森病、抗中风、抗缺血、抗抑郁和抗遗忘活性，并在阿尔茨海默病的实验模型中活跃。所述化合物的这些体内效应在腹腔内给药时的剂量范围为0.01至10毫克/千克。
• Solid-state linear polarized IR-spectroscopic and theoretical analysis of methioninamide ester amide of squaric acid diethyl ester
  作者：Emiliya Cherneva、Tsonko Kolev

  DOI：10.1016/j.molstruc.2006.06.009

  日期：2007.3

  Methioninamide ester amide of squaric acid (1) has been analyzed structurally and IR-spectroscopically by means of ab initio calculations and solid-state linear-polarized IR-spectroscopy (IR-LD) of oriented solid-samples as suspension in nematic liquid crystal. The obtained data are compared with known single crystal X-ray diffraction ones. The experimental IR-spectroscopic bands assignment in solid-state

  方酸的甲硫氨酰胺酯酰胺 (1) 已通过从头计算和固态线性偏振红外光谱 (IR-LD) 对作为向列液晶悬浮液的定向固体样品进行结构和红外光谱分析。将获得的数据与已知的单晶 X 射线衍射数据进行比较。还报告了固态中的实验红外光谱带分配，使用减差程序进行偏振红外光谱解释。
• Preparation and use of methionylmethionine as feed additive for fish and crustaceans
  申请人：Kobler Christoph

  公开号：US09095161B2

  公开（公告）日：2015-08-04

  An animal feed mixture containing DL-methionyl-DL-methionine and salts thereof for animals kept in aquacultures is provided. Methods for preparing DL-methionyl-DL-methionine of formula (I) and methods to fractionate the diasteriomeric forms obtained are also provided.

  提供了一种含有DL-甲硫氨酰-DL-甲硫氨酸及其盐的动物饲料混合物，适用于水产养殖中的动物。同时还提供了制备式(I)的DL-甲硫氨酰-DL-甲硫氨酸的方法以及分离所得对映异构体形式的方法。
• METHOD FOR PRODUCING alpha-AMINO ACID
  申请人：SHOWA DENKO K.K.

  公开号：US20190161434A1

  公开（公告）日：2019-05-30

  The present invention relates to a method for producing a specified α-amino acid, the method including allowing a specified α-amino acid amide and water to react with each other in the presence of a zirconium compound which contains zirconium and at least one metal element selected from the group consisting of lithium, nickel, copper, zinc, cesium, barium, hafnium, tantalum, cerium, and dysprosium.

  本发明涉及一种生产特定α-氨基酸的方法，该方法包括在存在含锆和来自锂、镍、铜、锌、铯、钡、铪、钽、铈和镝组成的金属元素中，使特定α-氨基酸酰胺和水相互反应。
• [DE] SUBSTITUIERTE 1,4,8-TRIAZASPIRO[4.5]DECAN-2-ON-VERBINDUNGEN<br/>[EN] SUBSTITUTED 1,4,8-TRIAZASPIRO[4.5]DECAN-2-ONE COMPOUNDS<br/>[FR] COMPOSES DE 1,4,8-TRIAZASPIRO[4.5]DECAN-2-ONE SUBSTITUES
  申请人：GRUENENTHAL GMBH

  公开号：WO2005095398A1

  公开（公告）日：2005-10-13

  Die vorliegende Erfindung betrifft substituierte 1,4,8,-Triazaspiro[4.5]decan-2-on-Verbindungen, Verfahren zu deren Herstellung, Arzneimittel enthaltend diese Verbindung sowie die Verwendung dieser Verbindungen zur Herstellung von Arzneimitteln.

  本发明涉及取代的1,4,8-三氮杂螺[4.5]癸烷-2-酮化合物，其制备方法，含有该化合物的药物，以及利用这些化合物制备药物的用途。