(R)-2-Amino-3-{3-[(R)-2-((R)-2-amino-2-carboxy-ethyldisulfanyl)-1-carboxy-ethylamino]-5-hydroxy-7-methyl-2,7-dihydro-[1,4]thiazino[2,3-e]indol-6-ylsulfanyl}-propionic acid | 196309-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-2-Amino-3-{3-[(R)-2-((R)-2-amino-2-carboxy-ethyldisulfanyl)-1-carboxy-ethylamino]-5-hydroxy-7-methyl-2,7-dihydro-[1,4]thiazino[2,3-e]indol-6-ylsulfanyl}-propionic acid
• CAS: 196309-91-8
• 化学式: C₂₀H₂₅N₅O₇S₄
• 分子量: 575.712
• InChiKey: JLTQSEVNDBCHIJ-DCAQKATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  36.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  213.49
• 氢给体数：
  7.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (R)-2-Amino-3-{3-[(R)-2-((R)-2-amino-2-carboxy-ethyldisulfanyl)-1-carboxy-ethylamino]-5-hydroxy-7-methyl-2,7-dihydro-[1,4]thiazino[2,3-e]indol-6-ylsulfanyl}-propionic acid 在 氢氧化钾 、 三(2-羰基乙基)磷盐酸盐 作用下， 生成
  参考文献：
  名称：

  Further Insights into the Oxidation Chemistry of Norepinephrine and Epinephrine in the Presence of Cysteine

  摘要：

  Oxidations of dopamine (DA), norepinephrine (NE), and epinephrine (EPI) at pH 7.4 in the presence of free L-cysteine (CySH) have been previously shown to generate a number of cysteinyl conjugates of these catecholaminergic neurotransmitters that serve as precursors of various dihydrobenzothiazines (DHBTs). In this investigation it is demonstrated that oxidations of NE or EPI, but not DA, in the presence of free CySH also generate three previously unknown DHBTs: 6,8-bis[(2-amino-2-carboxyethyl)thio]-3,4-dihydro-5-hydroxy-2H-1,4-benzothiazine-3-carboxylic acid (A), 6,7,8-tris[(2-amino-2-carboxyethyl)thio]-3,4-dihydro-5-hydroxy-2H-1,4-benzothiazine-3-carboxylic acid (B), and N-[9-[(2-amino-2-carboxyethyl)thio]-7-carboxy-3,6,7,8-tetrahydro-10-hydroxybenzo[1,2-b: 4,3-b']bis[1,4]thiazin-2-yl]-L-cystine (C). The beta-hydroxy side chain residues of NE and EPI are required in order to form A-C, hence explaining the fact that these compounds are not formed upon oxidation of DA in the presence of CySH. A further new product unique to the oxidation of EPI in the presence of CySH at pH 7.4 is N-[6-[(2-amino-2-carboxyethyl)thio]-2,7-dihydro-5-hydroxy-7-methylpyrrolo[2,3-h]-1,4-benzothiazin-3-yl]-L-cystine (D). Reactions pathways that account for formation of A-D are presented along with a discussion of their potential formation as aberrant metabolites in the brain in a number of neurodegenerative disorders. (C) 1997 Academic Press.

  DOI：

  10.1006/bioo.1997.1061
• 作为产物：
  描述：

  L-半胱氨酸 、 肾上腺素 生成 、 (R)-2-Amino-3-{3-[(R)-2-((R)-2-amino-2-carboxy-ethyldisulfanyl)-1-carboxy-ethylamino]-5-hydroxy-7-methyl-2,7-dihydro-[1,4]thiazino[2,3-e]indol-6-ylsulfanyl}-propionic acid 、 、 (R)-7-[(R)-2-((R)-2-Amino-2-carboxy-ethyldisulfanyl)-1-carboxy-ethylamino]-10-((R)-2-amino-2-carboxy-ethylsulfanyl)-9-hydroxy-1,2,3,6-tetrahydro-4,5-dithia-1,8-diaza-phenanthrene-2-carboxylic acid
  参考文献：
  名称：

  Further Insights into the Oxidation Chemistry of Norepinephrine and Epinephrine in the Presence of Cysteine

  摘要：

  Oxidations of dopamine (DA), norepinephrine (NE), and epinephrine (EPI) at pH 7.4 in the presence of free L-cysteine (CySH) have been previously shown to generate a number of cysteinyl conjugates of these catecholaminergic neurotransmitters that serve as precursors of various dihydrobenzothiazines (DHBTs). In this investigation it is demonstrated that oxidations of NE or EPI, but not DA, in the presence of free CySH also generate three previously unknown DHBTs: 6,8-bis[(2-amino-2-carboxyethyl)thio]-3,4-dihydro-5-hydroxy-2H-1,4-benzothiazine-3-carboxylic acid (A), 6,7,8-tris[(2-amino-2-carboxyethyl)thio]-3,4-dihydro-5-hydroxy-2H-1,4-benzothiazine-3-carboxylic acid (B), and N-[9-[(2-amino-2-carboxyethyl)thio]-7-carboxy-3,6,7,8-tetrahydro-10-hydroxybenzo[1,2-b: 4,3-b']bis[1,4]thiazin-2-yl]-L-cystine (C). The beta-hydroxy side chain residues of NE and EPI are required in order to form A-C, hence explaining the fact that these compounds are not formed upon oxidation of DA in the presence of CySH. A further new product unique to the oxidation of EPI in the presence of CySH at pH 7.4 is N-[6-[(2-amino-2-carboxyethyl)thio]-2,7-dihydro-5-hydroxy-7-methylpyrrolo[2,3-h]-1,4-benzothiazin-3-yl]-L-cystine (D). Reactions pathways that account for formation of A-D are presented along with a discussion of their potential formation as aberrant metabolites in the brain in a number of neurodegenerative disorders. (C) 1997 Academic Press.

  DOI：

  10.1006/bioo.1997.1061