N^Γ-hydroxy-N^δ-methyl-L-arginine | 863987-43-3

• 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
• 英文名称: N^Γ-hydroxy-N^δ-methyl-L-arginine
• 英文别名: N^ω-hydroxy-N^δ-methyl-L-arginine；δMHA；(2S)-2-amino-5-[[(Z)-N'-hydroxycarbamimidoyl]-methylamino]pentanoic acid
• CAS: 863987-43-3
• 化学式: C₇H₁₆N₄O₃
• 分子量: 204.229
• InChiKey: AUQNEMXAWPGGNP-YFKPBYRVSA-N

物化性质

• 沸点：
  391.3±52.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N^Γ-hydroxy-N^δ-methyl-L-arginine 在 magnesium chloride phosphate buffer 、 还原型辅酶II(NADPH)四钠盐 作用下， 反应 0.5h， 生成 N^δ-cyano-N^δ-methyl-L-ornithine
  参考文献：
  名称：

  Nδ-Methylated l-arginine derivatives and their effects on the nitric oxide generating system

  摘要：

  So far N-delta-methyl-L-arginine (MA) is only detected in yeast cells. Assuming that MA also exists in mammalians we examined possible physiological effects of N-delta-methylated L-arginine derivatives on the nitric oxide generating system, that is, nitric oxide synthase (NOS), arginase and dimethylarginine dimethylaminohydrolase (DDAH). N-delta-methyl-L-citrulline (MC) turned out to be a weak non-specific inhibitor of nitric oxide synthases. Moreover, MA is hydroxylated by all human NOS isoforms to N-hydroxy-N-delta-methyl-L-arginine (NHAM) but not converted further. This hydroxylated intermediate, however, was detected to be a potent inhibitor of bovine liver arginase with a K-i of 17.1 +/- 2.2 mu M. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.066
• 作为产物：
  描述：

  N^δ-methyl-L-ornithine hydrochloride 在 盐酸羟胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 为溶剂， 反应 53.0h， 生成 N^Γ-hydroxy-N^δ-methyl-L-arginine
  参考文献：
  名称：

  l-Arginine analogs as alternate substrates for nitric oxide synthase

  摘要：

  The L-arginine analogs, N-delta-methyl-L-arginine (delta MA) and L-canavanine, were used to probe the role of the N-delta nitrogen of L-arginine in the reaction catalyzed by nitric oxide synthase (NOS). delta MA was synthesized and found to be a partial alternate substrate and a weak, reversible inhibitor of NOS with a K-i equal to 1.4 mM. delta MA undergoes hydroxylation; however, it is not converted further, hence it functions as a partial substrate. L-Canavanine was converted to an L-homoserine presumably via initial hydroxylation and decomposition. The mechanism of this reaction and products of this reaction were not probed further. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.088

文献信息

• l-Arginine analogs as alternate substrates for nitric oxide synthase
  作者：Scott D. Luzzi、Michael A. Marletta

  DOI：10.1016/j.bmcl.2005.05.088

  日期：2005.9

  The L-arginine analogs, N-delta-methyl-L-arginine (delta MA) and L-canavanine, were used to probe the role of the N-delta nitrogen of L-arginine in the reaction catalyzed by nitric oxide synthase (NOS). delta MA was synthesized and found to be a partial alternate substrate and a weak, reversible inhibitor of NOS with a K-i equal to 1.4 mM. delta MA undergoes hydroxylation; however, it is not converted further, hence it functions as a partial substrate. L-Canavanine was converted to an L-homoserine presumably via initial hydroxylation and decomposition. The mechanism of this reaction and products of this reaction were not probed further. (c) 2005 Elsevier Ltd. All rights reserved.
• Nδ-Methylated l-arginine derivatives and their effects on the nitric oxide generating system
  作者：Jürke Kotthaus、Dennis Schade、Katrin Töpker-Lehmann、Eric Beitz、Bernd Clement

  DOI：10.1016/j.bmc.2007.11.066

  日期：2008.3

  So far N-delta-methyl-L-arginine (MA) is only detected in yeast cells. Assuming that MA also exists in mammalians we examined possible physiological effects of N-delta-methylated L-arginine derivatives on the nitric oxide generating system, that is, nitric oxide synthase (NOS), arginase and dimethylarginine dimethylaminohydrolase (DDAH). N-delta-methyl-L-citrulline (MC) turned out to be a weak non-specific inhibitor of nitric oxide synthases. Moreover, MA is hydroxylated by all human NOS isoforms to N-hydroxy-N-delta-methyl-L-arginine (NHAM) but not converted further. This hydroxylated intermediate, however, was detected to be a potent inhibitor of bovine liver arginase with a K-i of 17.1 +/- 2.2 mu M. (C) 2007 Elsevier Ltd. All rights reserved.