1-(2'-Pyrrolidinethion-3'-yl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid | 128595-56-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-(2'-Pyrrolidinethion-3'-yl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
• 英文别名: 1-(2-sulfanylidenepyrrolidin-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid
• CAS: 128595-56-2
• 化学式: C₁₆H₁₇N₃O₂S
• 分子量: 315.396
• InChiKey: YHAYSIGUKKXZJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2'-Pyrrolidinethion-3'-yl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid 在 potassium chromate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 0.02h， 生成 1-(4'-amino-3'-butenal-2'-yl)-β-carboline
  参考文献：
  名称：

  Ozawa, Yoshio; Uda, Yasushi; Kawakishi, Shunro, Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 1, p. 144

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(甲硫基)-3-丁烯基异硫氰酸酯 、 L-色氨酸 反应 2.0h， 以70 mg的产率得到1-(2'-Pyrrolidinethion-3'-yl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid
  参考文献：
  名称：

  Ozawa, Yoshio; Uda, Yasushi; Kawakishi, Shunro, Agricultural and Biological Chemistry, 1990, vol. 54, # 7, p. 1849 - 1851

  摘要：

  DOI：

文献信息

• 2-[3-(2-Thioxopyrrolidin-3-ylidene)methyl]-tryptophan, a Novel Yellow Pigment in Salted Radish Roots
  作者：Hiroki MATSUOKA、Asaka TAKAHASHI、Yoshio OZAWA、Yoichi YAMADA、Yasushi UDA、Shunro KAWAKISHI

  DOI：10.1271/bbb.66.1450

  日期：2002.1

  The structure of the yellow pigment found in salted radish roots was studied. It was found that 1-(2-thioxopyrrolidin-3-yl)-1,2,3,4-tetrahydro-β-carboline-3- carboxylic acid (TPCC) was unstable under neutral pH, and was easily converted into the yellow pigment. The yellow pigment was isolated and identified as 2-[3-(2-thioxopyrrolidin-3-ylidene)methyl]-tryptophan (TPMT) by IR, MS, 1H-, and 13C-NMR spectroscopy. In addition, we proved that this compound was the main yellow pigment in salted radish roots. This compound induced no mutagenicity in Salmonella typhimurium TA98 and TA100, either with or without prior activation.

  研究了盐渍萝卜根中黄色素的结构。研究发现，1-(2-硫酮吡咯烷-3-基)-1,2,3,4-四氢-β-咔啉-3-羧酸（TPCC）在中性 pH 值下不稳定，很容易转化成黄色素。通过红外光谱、质谱、1H- 和 13C-NMR 光谱，我们分离并鉴定出这种黄色色素为 2-[3-(2-硫酮吡咯烷-3-亚基)甲基]-色氨酸（TPMT）。此外，我们还证明该化合物是盐渍萝卜根中的主要黄色素。无论是否事先活化，该化合物都不会诱发鼠伤寒沙门氏菌 TA98 和 TA100 的致突变性。
• Occurrence of Stereoisomers of 1-(2′-Pyrrolidinethione-3′-yl)-1,2,3,4- tetrahydro-β-carboline-3-carboxylic Acid in Fermented Radish Roots and Their Different Mutagenic Properties
  作者：Yoshio OZAWA、Yasushi UDA、Hiroki MATSUOKA、Masako ABE、Shunro KAWAKISHI、Toshihiko OSAWA

  DOI：10.1271/bbb.63.216

  日期：1999.1

  Stereoisomers of the tetrahydro-β-carboline derivative, 1-(2′-pyrrolidinethione-3′-yl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (PTCC), were formed from L-tryptophan with 4-methylthio-3-butenyl isothiocyanate, and their mutagenic properties and contents in different types of the radish products were studied. The isomers were identified as (1S*, 3S*, 3′R*)- and (1R*, 3S*, 3′R*)-PTCCs; the former was found as the major compound but had no mutagenic activity, while the latter was mutagenic toward Salmonella typhimurium TA 98 in the presence of a rat microsomal fraction. Both (1S*, 3S*, 3′R*)- and (1R*, 3S*, 3′R*)-PTCC were detected in a ratio of about 4:1 in a product fermented for 8 months, but only a trace was apparent in products manufactured within a few weeks.