5-hydroxy-N-formylkynurenine | 73637-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-hydroxy-N-formylkynurenine
• 英文别名: L-tryptophan；L-Trp；5-hydroxy-N-formyl-L-kynurenine；(2S)-2-amino-4-(2-formamido-5-hydroxyphenyl)-4-oxobutanoic acid
• CAS: 73637-65-7
• 化学式: C₁₁H₁₂N₂O₅
• 分子量: 252.227
• InChiKey: LSTOUSIIVKMJBU-QMMMGPOBSA-N

物化性质

• 沸点：
  659.8±55.0 °C(Predicted)
• 密度：
  1.502±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-hydroxy-N-formylkynurenine 在 高氯酸 作用下， 生成 5-hydroxykynurenine
  参考文献：
  名称：

  N（1）-氟烷基色氨酸类似物：吲哚胺2,3-二加氧酶的潜在底物的合成和体外研究。

  摘要：

  吲哚胺2，3-二加氧酶（hIDO）是一种酶，可通过犬尿氨酸途径催化1-色氨酸吲哚环的氧化裂解，从而在炎症和肿瘤组织中发挥免疫抑制特性。1-（2-氟乙基）-色氨酸（1-FETrp）和1-（（1-（2-氟乙基）-1H-1,2,3-三唑-4-基）甲基）-色氨酸的合成，两个在此描述了N（1）-氟代烷基色氨酸衍生物。用hIDO的这两种新的潜在底物进行的体外酶分析表明1-FETrp是hIDO的良好而特异性的底物。因此，其放射性同位素异构体1-[（（18）F] FETrp）应该成为可视化肿瘤和炎性组织和/或验证新的潜在抑制剂的分子选择。

  DOI：

  10.1021/ml500385d
• 作为产物：
  描述：

  5-羟基-L-色氨酸 在 rhIDO 作用下， 反应 1.0h， 生成 5-hydroxy-N-formylkynurenine
  参考文献：
  名称：

  N（1）-氟烷基色氨酸类似物：吲哚胺2,3-二加氧酶的潜在底物的合成和体外研究。

  摘要：

  吲哚胺2，3-二加氧酶（hIDO）是一种酶，可通过犬尿氨酸途径催化1-色氨酸吲哚环的氧化裂解，从而在炎症和肿瘤组织中发挥免疫抑制特性。1-（2-氟乙基）-色氨酸（1-FETrp）和1-（（1-（2-氟乙基）-1H-1,2,3-三唑-4-基）甲基）-色氨酸的合成，两个在此描述了N（1）-氟代烷基色氨酸衍生物。用hIDO的这两种新的潜在底物进行的体外酶分析表明1-FETrp是hIDO的良好而特异性的底物。因此，其放射性同位素异构体1-[（（18）F] FETrp）应该成为可视化肿瘤和炎性组织和/或验证新的潜在抑制剂的分子选择。

  DOI：

  10.1021/ml500385d

文献信息

• Human indoleamine 2,3-dioxygenase-2 has substrate specificity and inhibition characteristics distinct from those of indoleamine 2,3-dioxygenase-1
  作者：Georgios Pantouris、Martynas Serys、Hajime J. Yuasa、Helen J. Ball、Christopher G. Mowat

  DOI：10.1007/s00726-014-1766-3

  日期：2014.9

  Indoleamine 2,3-dioxygenase-2 (IDO2) is one of three enzymes (alongside tryptophan 2,3-dioxygenase and indoleamine 2,3-dioxygenase (IDO1)) that catalyse dioxygenation of L-tryptophan as the first step in the kynurenine pathway. Despite the reported expression of IDO2 in tumours, some fundamental characteristics of the enzyme, such as substrate specificity and inhibition selectivity, are still to be clearly defined. In this study, we report the kinetic and inhibition characteristics of recombinant human IDO2. Choosing from a series of likely IDO2 substrates, we screened 54 tryptophan derivatives and tryptophan-like molecules, and characterised the 8 with which the enzyme was most active. Specificity of IDO2 for the two isomers of 1-methyltryptophan was also evaluated and the findings compared with those obtained in other studies on IDO2 and IDO1. Interestingly, IDO2 demonstrates behaviour distinct from that of IDO1 in terms of substrate specificity and affinity, such that we have identified tryptophan derivatives that are mutually exclusive as substrates for IDO1 and IDO2. Our results support the idea that the antitumour activity of 1-Me-D-Trp is unlikely to be related with competitive inhibition of IDO2, and also imply that there are subtle differences in active site structure in the two enzymes that may be exploited in the development of specific inhibitors of these enzymes, a route which may prove important in defining their role(s) in cancer.
• Nakagawa, Masako; Yokoyama, Yukio; Kato, Shiro, Heterocycles, 1984, vol. 22, # 1, p. 59 - 62
  作者：Nakagawa, Masako、Yokoyama, Yukio、Kato, Shiro、Hino, Tohru

  DOI：——

  日期：——
• <i>N</i>¹-Fluoroalkyltryptophan Analogues: Synthesis and <i>in vitro</i> Study as Potential Substrates for Indoleamine 2,3-Dioxygenase
  作者：Jean Henrottin、Astrid Zervosen、Christian Lemaire、Frédéric Sapunaric、Sophie Laurent、Benoit Van den Eynde、Serge Goldman、Alain Plenevaux、André Luxen

  DOI：10.1021/ml500385d

  日期：2015.3.12

  tryptophan, two N (1)-fluoroalkylated tryptophan derivatives, are described here. In vitro enzymatic assays with these two new potential substrates of hIDO show that 1-FETrp is a good and specific substrate of hIDO. Therefore, its radioactive isotopomer, 1-[(18)F]FETrp, should be a molecule of choice to visualize tumoral and inflammatory tissues and/or to validate new potential inhibitors.

  吲哚胺2，3-二加氧酶（hIDO）是一种酶，可通过犬尿氨酸途径催化1-色氨酸吲哚环的氧化裂解，从而在炎症和肿瘤组织中发挥免疫抑制特性。1-（2-氟乙基）-色氨酸（1-FETrp）和1-（（1-（2-氟乙基）-1H-1,2,3-三唑-4-基）甲基）-色氨酸的合成，两个在此描述了N（1）-氟代烷基色氨酸衍生物。用hIDO的这两种新的潜在底物进行的体外酶分析表明1-FETrp是hIDO的良好而特异性的底物。因此，其放射性同位素异构体1-[（（18）F] FETrp）应该成为可视化肿瘤和炎性组织和/或验证新的潜在抑制剂的分子选择。