L-去甲精氨酸 | 14191-90-3

• 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-去甲精氨酸
• 英文名称: (S)-2-amino-4-guanidinobutanoic acid
• 英文别名: arginine；(S)-2-amino-4-guanidino-butyric acid；(S)-2-Amino-4-guanidino-buttersaeure；γ-Guanidino-L-α-aminobuttersaeure；L-2-Amino-4-guanidino-buttersaeure；L-Norarginine；(2S)-2-amino-4-(diaminomethylideneamino)butanoic acid
• CAS: 14191-90-3
• 化学式: C₅H₁₂N₄O₂
• 分子量: 160.176
• InChiKey: IFPQOXNWLSRZKX-VKHMYHEASA-N

物化性质

• 沸点：
  357.6±52.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-去甲精氨酸 、 丝裂霉素 A 在 三乙胺 作用下， 以 水 为溶剂， 反应 1.0h， 以71%的产率得到(S)-2-(((1aS,8S,8aR,8bS)-8-((carbamoyloxy)methyl)-8a-methoxy-5-methyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2',3':3,4]pyrrolo[1,2-a]indol-6-yl)amino)-4-guanidinobutanoic acid
  参考文献：
  名称：

  具有增加的金属络合能力的丝裂霉素C类似物。

  摘要：

  合成了二十三种旨在增加金属络合能力的丝裂霉素C类似物，并在小鼠中针对P388白血病进行了测试。由这种金属引起的紫外线吸收光谱的变化揭示了它们络合Cu（II）的能力。在抗肿瘤试验中，一种类似物显然比丝裂霉素C更有活性，另外两种具有良好的活性。抗肿瘤活性与Cu（II）络合能力之间的相关性尚不明确。活性最高的化合物不是络合剂，或者是它们的络合剂仅限于N7上的2-（2-吡啶基）烷基型取代基。N7上的多种氨基酸取代基仅显示出较弱的抗肿瘤活性。

  DOI：

  10.1021/jm00159a033
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 L-去甲精氨酸
  参考文献：
  名称：

  Takagi et al., Chemical and pharmaceutical bulletin, 1959, vol. 7, p. 616

  摘要：

  DOI：

文献信息

• Discovery of a septin-4 covalent binder with antimetastatic activity in a mouse model of melanoma
  作者：Federica Blua、Chiara Monge、Simone Gastaldi、Nausicaa Clemente、Stefania Pizzimenti、Loretta Lazzarato、Rebecca Senetta、Serena Vittorio、Casimiro Luca Gigliotti、Elena Boggio、Umberto Dianzani、Giulio Vistoli、Alessandra Anna Altomare、Giancarlo Aldini、Chiara Dianzani、Elisabetta Marini、Massimo Bertinaria

  DOI：10.1016/j.bioorg.2024.107164

  日期：2024.3

  find the structural determinants of activity, and to identify the cellular target responsible of the downstream anti-metastatic effects observed. New compounds synthesized were able to inhibit in vitro B16-F10 melanoma cell invasiveness, and one selected compound, CM365, showed in vivo anti-metastatic effects in a lung metastasis mouse model of melanoma. Septin-4 was identified as the most likely molecular

  癌症通过转移过程扩散是肿瘤相关死亡的主要原因之一。转移是一种复杂的现象，涉及从细胞代谢改变到细胞和组织生物物理表型变化的多种途径。在寻找新的有效抗转移剂的过程中，我们调节了先导化合物 AA6 的化学结构，以找到活性的结构决定因素，并确定负责观察到的下游抗转移作用的细胞靶点。合成的新化合物能够在体外抑制 B16-F10 黑色素瘤细胞的侵袭性，并且一种选定的化合物 CM365 在黑色素瘤肺转移小鼠模型中显示出体内抗转移作用。 Septin-4 被确定为最有可能导致这些效应的分子靶点。这项研究表明，CM365 是一种有前途的预防转移分子，单独使用或与通常用于癌症治疗的药物（例如紫杉醇）联合使用都非常有效。
• Selective Substrate-Based Inhibitors of Mammalian Dimethylarginine Dimethylaminohydrolase
  作者：Sharon Rossiter、Caroline L. Smith、Mohammed Malaki、Manasi Nandi、Herpreet Gill、James M. Leiper、Patrick Vallance、David L. Selwood

  DOI：10.1021/jm050187a

  日期：2005.7.1

  The enzyme DDAH metabolizes methylarginines that are inhibitors of nitric oxide synthase (NOS). Substrate-based inhibitors of mammalian DDAH have been synthesized, with optimization to give selective inhibition of DDAH with no significant direct effect on NOSs. These are the first examples of reversible DDAH inhibitors with significant activity and selectivity. In vivo administration increases plasma ADMA levels, giving proof of concept that these inhibitors can be used to probe the physiological effects of DDAH inhibition, with potential for pharmaceutical use of DDAH inhibitors in diseases where excess NO production is implicated.
• Effects of Arginine Homologues and other Guanidino Compounds on the ATP Level and Glucose Oxidation in Isolated Fat Cells
  作者：Friedemann Schwegler、Wieland Stock

  DOI：10.1515/bchm2.1975.356.s1.839

  日期：1975.1

  The arginine homologues 2-amino-3-guanidinopropionic acid, 2-amino-4-guanidino-butyric acid and 2-amino-6-guanidinocaproic acid (= homoarginine) were synthesized and transformed into their methyl esters. The latter, together with arginine methyl esters. The latter, together with arginine methyl ester, arginine diethylamide and some guanidino compounds without the arginyl structure (agmatine, isopentyl-guanidine and n-butylbiguanide) were examined with regard to their behaviour on isolated fat cells, concerning the adrenalin-induced depression of the ATP level and the stimulation of glucose oxidation. The homoarginyl and arginyl derivatives counteracted the effect of adrenalin by re-elevating the ATP level, and thus they exerted an insulin-like activity. The esters were slightly active, whereas the arginine diethylamide and agmatine had a marked effect. The shorter homologues of arginine were totally inactive. However isopentyl-guanidine and butylbiguanide followed the effect of adrenalin: they additionally lowered the ATP level and therefore they acted in opposition to insulin. For comparative reasons the same compounds were tested with regard to their effects on glucose oxidation. The results were consistent with those quoted above: the homoarginyl and arginyl derivatives (agmatine included) forced the glucose oxidation similarly to insulin, the shorter homologues were inactive, isopentylguanidine and butylbiguanide decreased it.
• Takagi et al., Chemical and pharmaceutical bulletin, 1959, vol. 7, p. 616
  作者：Takagi et al.

  DOI：——

  日期：——
• Izumiya; Kitagawa, Nippon Kagaku Zasshi, 1958, vol. 79, p. 65,66
  作者：Izumiya、Kitagawa

  DOI：——

  日期：——