L-蛋氨酰胺 | 16120-92-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他保护氨基酸
• 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: L-蛋氨酰胺
• 英文名称: (S)-methioninamide hydrochloride
• 英文别名: L-Methionine amide hydrochloride；Met-NH2 hydrochloride；(S)-Met-NH2*HCl；H-Met-NH2 hydrochloride；(2S)-2-amino-4-(methylthio)butanamide hydrochloride；(2S)-2-amino-4-(methylthio)-butanamide, monohydrochloride；L-methioninamide hydrochloride；H-methionine-NH2 HCl；L-Met-NH2*HCl；[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]azanium;chloride
• CAS: 16120-92-6
• 化学式: C₅H₁₃N₂OS*Cl
• mdl: MFCD00039084
• 分子量: 184.69
• InChiKey: PWCBMJHINDTXGV-WCCKRBBISA-N

物化性质

• 熔点：
  160-162 °C (decomp)(Solv: ethanol (64-17-5))

计算性质

• 辛醇/水分配系数(LogP)：
  -0.73
• 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

安全信息

• WGK Germany：
  3
• 海关编码：
  29309099
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  L-蛋氨酰胺 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (2S)-2-amino-5-thiahexylamine
  参考文献：
  名称：

  Asymmetric trimethylsilylcyanation of aldehydes catalyzed by chiral salen TiIV complexes with theC 1 symmetry

  摘要：

  Asymmetric trimethylsilylcyanation of a number of aromatic and aliphatic aldehydes catalyzed by chiral Ti-IV complexes prepared in situ from Ti(OPri)(4) and (1S)-[N,N'-bis(2'-hydroxy-3'-tert-butylbenzylidene)]-1,2-diaminoalkanes gives products with (S)-absolute configurations.

  DOI：

  10.1007/bf02503790
• 作为产物：
  描述：

  Boc-L-蛋氨酸 在 盐酸 、 ammonium hydroxide 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 生成 L-蛋氨酰胺
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Dehydrophenylalanine Containing Substance P Fragments

  摘要：

  合成了与物质P的C端片段（6-11）和（4-11）相对应的肽段，这些片段包含一个假定的β-转角，采用溶液相的方法。合成了物质P的类似物，其中第8位的苯丙氨酸残基被脱氢苯丙氨酸（ΔPhe）替代，第9位的甘氨酸残基被丙氨酸、缬氨酸、肌氨酸（N–Me–Gly）和α-氨基异丁酸替代。在两个类似物[8-ΔPhe, 9-Sar]–SP (4-11) (5)和[5,8-ΔPhe, 9-Aib]–SP (4-11) (7)中，第5位的谷氨酰胺残基也被ΔPhe替代。这些类似物在豚鼠回肠制备中（体外）评估了其引起平滑肌收缩的能力，并在以氨基甲酸酯麻醉的雌性大鼠中评估了其降血压活性。在六肽系列中，[8-ΔPhe]–SP (6-11) (1)和[8-ΔPhe, 9-Sar]–SP (6-11) (4)在两项实验中均显示出显著的活性。八肽[5,8-ΔPhe, 9-Sar]–SP (4-11) (5)在第5和第8位具有ΔPhe残基并在第9位含有肌氨酸，发现其在体外和体内系统中是最有效的类似物。

  DOI：

  10.1246/bcsj.65.3412

文献信息

• New Bioactive Zinc(II) Complexes with Peptides and Their Derivatives: Synthesis, Structure, and In Vitro Insulinomimetic Activity
  作者：Eriko Ueda、Yutaka Yoshikawa、Noriko Kishimoto、Makoto Tadokoro、Hiromu Sakurai、Naemi Kajiwara、Yoshitane Kojima

  DOI：10.1246/bcsj.77.981

  日期：2004.5

  Four Zn(II) complexes with dipeptides and three new Zn(II) complexe; with pseudo-tripeptides were prepared and a complex, [Zn(glythr) 2 ] n , was revealed to have a polymeric structure by X-ray structure analysis. The ligand, glythr - , acts as a bridging ligand completely, a monodentate oxygen atom of the terminal carboxyl group of threonine residue and a didentate ligand containing the nitrogen and

  四种含二肽的 Zn(II) 络合物和三种新的 Zn(II) 络合物；制备了具有假三肽的复合物，[Zn(glythr) 2 ] n ，通过 X 射线结构分析显示具有聚合物结构。配体glythr - 完全充当桥连配体，苏氨酸残基末端羧基的单齿氧原子和含有甘氨酸之一的氮和氧原子的双齿配体。因为 Zn 2 + 离子具有扭曲的六配位八面体几何形状，它与两个末端羧基和两个双齿配体结合。此外，发现与硫酸锌相比，所有 Zn(II) 复合物都具有较高的体外胰岛素模拟活性，这是通过抑制已用肾上腺素（肾上腺素）处理的分离大鼠脂肪细胞中的游离脂肪酸释放来估计的。
• 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。
• Mild and Chemoselective Thioacylation of Amines Enabled by the Nucleophilic Activation of Elemental Sulfur
  作者：Masato Saito、Sho Murakami、Takeshi Nanjo、Yusuke Kobayashi、Yoshiji Takemoto

  DOI：10.1021/jacs.0c03256

  日期：2020.5.6

  for the thioacylation of amines using α-ketoacids and elemental sulfur has been developed. The key to success for this transformation is the nucleophilic activation of elemental sulfur by thiols such as 1-dodecanethiol. A variety of functional groups, including unprotected hydroxyl, carboxyl, amide, sulfide, and tertiary amine moieties are tolerated under the applied reaction conditions. To demonstrate

  已经开发了一种使用 α-酮酸和元素硫对胺进行硫代酰化的温和且化学选择性的方法。这种转化成功的关键是硫醇（如 1-十二烷硫醇）对元素硫的亲核活化。在所应用的反应条件下，可以耐受各种官能团，包括未保护的羟基、羧基、酰胺、硫化物和叔胺部分。为了证明与使用 Lawesson 试剂或 P2S5 的传统 OS 交换反应相比，该方法的优势，将硫代酰胺部分特定地引入到生物活性化合物中。
• [EN] CATHEPSIN INHIBITORS<br/>[FR] INHIBITEURS DE LA CATHEPSINE
  申请人：MERCK FROSST CANADA INC

  公开号：WO2005021487A1

  公开（公告）日：2005-03-10

  This invention relates to a novel class of compounds, represented by the formula (I) below, wherein the meanings of R1, R2, R3 and R4 are indicated therein, which are cysteine protease inhibitors, including but not limited to, inhibitors of cathepsins K, L, S and B. These compounds are useful for treating diseases in which inhibition of bone resorption is indicated, such as osteoporosis, osteoarthritis and rheumatoid arthritis.

  这项发明涉及一类新型化合物，由下式（I）表示，其中R1、R2、R3和R4的含义已在其中指示，这些化合物是半胱氨酸蛋白酶抑制剂，包括但不限于对卡特普辛K、L、S和B的抑制剂。这些化合物对于治疗需要抑制骨吸收的疾病非常有用，如骨质疏松症、骨关节炎和类风湿性关节炎。
• Synthesis and Biological Evaluation of Dehydrophenylalanine Containing Substance P Fragments
  作者：Paramjeet Kaur、Gyanedra Kumar Patnaik、Ram Raghubir、Virander Singh Chauhan

  DOI：10.1246/bcsj.65.3412

  日期：1992.12

  Peptide fragments of Substance P corresponding to the C-terminal segments (6-11) and (4-11), which contain a putative β-turn, were synthesised using solution phase methodology. Analogs of Substance P were synthesised where the phenylalanine residue at position 8 was replaced by dehydrophenylalanine (ΔPhe) and the glycine residue in position 9 was replaced by alanine, valine, sarcosine (N–Me–Gly) and α-aminoisobutyric acid. In two of the analogs [8-ΔPhe, 9-Sar]–SP (4-11) (5) and [5,8-ΔPhe, 9-Aib]–SP (4-11) (7) glutamine residue at position 5 was also substituted by ΔPhe. These analogs were evaluated for their ability to cause smooth muscle contraction in guinea pig ileum preparation (in vitro) and for hypotensive activity (in vivo) in female rats anesthetized with urethane. In the hexapeptide series [8-ΔPhe]–SP (6-11) (1) and [8-ΔPhe, 9-Sar]–SP (6-11) (4) showed significant activity in both the assays. Octapeptide [5,8-ΔPhe, 9-Sar]–SP (4-11) (5) with ΔPhe residue in positions 5 and 8 and sarcosine in position 9 was found to be the most potent analog both in vitro and in vivo systems.

  合成了与物质P的C端片段（6-11）和（4-11）相对应的肽段，这些片段包含一个假定的β-转角，采用溶液相的方法。合成了物质P的类似物，其中第8位的苯丙氨酸残基被脱氢苯丙氨酸（ΔPhe）替代，第9位的甘氨酸残基被丙氨酸、缬氨酸、肌氨酸（N–Me–Gly）和α-氨基异丁酸替代。在两个类似物[8-ΔPhe, 9-Sar]–SP (4-11) (5)和[5,8-ΔPhe, 9-Aib]–SP (4-11) (7)中，第5位的谷氨酰胺残基也被ΔPhe替代。这些类似物在豚鼠回肠制备中（体外）评估了其引起平滑肌收缩的能力，并在以氨基甲酸酯麻醉的雌性大鼠中评估了其降血压活性。在六肽系列中，[8-ΔPhe]–SP (6-11) (1)和[8-ΔPhe, 9-Sar]–SP (6-11) (4)在两项实验中均显示出显著的活性。八肽[5,8-ΔPhe, 9-Sar]–SP (4-11) (5)在第5和第8位具有ΔPhe残基并在第9位含有肌氨酸，发现其在体外和体内系统中是最有效的类似物。