L-色氨酸-D5 | 62595-11-3

• 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
• 中文名称: L-色氨酸-D5
• 英文名称: [1,4,5,6,7-2H]-L-tryptophan
• 英文别名: (S)-[2',4',5',6',7'-D5]-tryptophan；<2,4,5,6,7-2H5>-L-tryptophan；L-<2,4,5,6,7-D5>-tryptophan；L-[2,4,6,5,6,7-(2)H5]-tryptophan；L-tryptophan-indole-d₅；L-tryptophan-(d₅₎；d₅-L-Trp；L-Tryptophan-d5；(2S)-2-amino-3-(2,4,5,6,7-pentadeuterio-1H-indol-3-yl)propanoic acid
• CAS: 62595-11-3
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 209.189
• InChiKey: QIVBCDIJIAJPQS-HLTLGYGQSA-N

物化性质

• 熔点：
  280-285 °C (dec.)(lit.)
• 溶解度：
  酸水溶液（微溶）、碱水溶液（微溶）、甲醇（微溶、超声处理、

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.1
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• WGK Germany：
  2
• 储存条件：
  | 2-8°C |

反应信息

• 作为反应物：
  描述：

  L-色氨酸-D5 在 catalase 作用下， 反应 2.0h， 以20%的产率得到(Deuteroindolyl-3)-brenztraubensaeure
  参考文献：
  名称：

  Biosynthetic Origin of BE-10988 in Streptomyces sp. BA10988

  摘要：

  The biosynthetic origin of the tumor-inhibitory derivative, BE-10988, was studied in Streptomyces sp. BA10988 by retrobiosynthetic NMR analysis using [U-C-13(6)]glucose as a precursor. The isotopologue compositions of the indole moieties of BE-10988 and tryptophan were virtually identical. This indicates that tryptophan or a closely related metabolite served as a biosynthetic precursor of BE-10988 in analogy to the biosynthetic pathway of camalexin, a structurally related phytoalexin in Arabidopsis thaliana. Labeling experiments with [U-(C8N)-C-13-N-15]indole, L-[ring-H-2(5)]tryptophan, or L-[U-(C3N)-C-13-N-15]cysteine confirmed this hypothesis. However, transfer of the label from [ring-H-2(5)]indole pyruvic acid, but not from the known camalexin precursor, [ring-H-2(5)]indole-3-acetaidoxime, showed that plants and bacteria have evolved independent mechanisms of tryptophan modification in the biosynthesis of thiazolylindole derivatives.

  DOI：

  10.1021/jo800375u
• 作为产物：
  描述：

  L-色氨酸 在 diclazuril 、 巯基乙酸 作用下， 以 重水 为溶剂， 反应 4.0h， 以99%的产率得到L-色氨酸-D5
  参考文献：
  名称：

  萤火虫Cypridina hilgendorfii中的萤光素生物合成：L-色氨酸是Cypridina luciferin中的一种成分

  摘要：

  使用在吲哚环上用氘标记的l-色氨酸对海洋原螯虾甲壳类的Cypridina（Vargula）hilgendorfii进行的饲喂实验表明，将标记的l-色氨酸作为一种成分掺入到Cypridina luciferin中，这些动物能够合成出一种荧光素。从头合成途径。

  DOI：

  10.1016/s0040-4039(02)00257-5

文献信息

• Hydrogen/deuterium exchange of cross-linkable α-amino acid derivatives in deuterated triflic acid
  作者：Lei Wang、Yuta Murai、Takuma Yoshida、Masashi Okamoto、Katsuyoshi Masuda、Yasuko Sakihama、Yasuyuki Hashidoko、Yasumaru Hatanaka、Makoto Hashimoto

  DOI：10.1080/09168451.2014.917267

  日期：2014.7.3

  hydrogen/deuterium exchange (H/D exchange) of cross-linkable α-amino acid derivatives with deuterated trifluoromethanesulfonic acid (TfOD). H/D exchange with TfOD was easily applied to o-catechol containing phenylalanine (DOPA) within an hour. A partial H/D exchange was observed for trifluoromethyldiazirinyl (TFMD) phenylalanine derivatives. N-Acetyl-protected natural aromatic α-amino acids (Tyr and Trp)

  在本文中，我们在这里报告了可氘化三氟甲磺酸（TfOD）的可交联α-氨基酸衍生物的氢/氘交换（H / D交换）。与TfOD的H / D交换很容易在一个小时内应用于含邻苯二酚的苯丙氨酸（DOPA）。观察到三氟甲基重氮基（TFMD）苯丙氨酸衍生物的部分H / D交换。N-乙酰基保护的天然芳香族α-氨基酸（Tyr和Trp）在H / D交换中比未保护的氨基酸更有效。N-乙酰化的TFMD苯丙氨酸衍生物比未保护的衍生物具有更高的H / D交换率。一种有效的可氘化的可交联α-氨基酸衍生物的氘化方法，对于通过质谱分析生物活性肽和蛋白质的生物学功能将是有用的。
• The biosynthesis of the mould metabolites roquefortine and aszonalenin from L-[2,4,5,6,7-2H5]Tryptophan
  作者：Balkrishen Bhat、David M. Harrison、H. Maxine Lamont

  DOI：10.1016/s0040-4020(01)81556-8

  日期：1993.1

  L-[2,4,5,6,7-2H5]Tryptophan was incorporated into roquefortine 2 by Penicillium roqueforti and aszonalenin 3 by Aspergillus zonatus with retention in each case of five deuterium atoms; that 5a-hydrogen of both metabolites is derived from the 2-hydrogen of tryptophan

  大号- [2,4,5,6,7- 2 ħ 5 ]色氨酸掺入roquefortine 2由娄地青霉和aszonalenin 3由曲霉zonatus与五个氘原子的每种情况下，保留; 两种代谢物的5a氢都来自色氨酸的2氢
• In Vitro Stepwise Reconstitution of Amino Acid Derived Vinyl Isocyanide Biosynthesis: Detection of an Elusive Intermediate
  作者：Wei-chen Chang、Dev Sanyal、Jhih-Liang Huang、Kuljira Ittiamornkul、Qin Zhu、Xinyu Liu

  DOI：10.1021/acs.orglett.7b00258

  日期：2017.3.3

  and AmbI2) and the detection of an elusive intermediate (S)-3-(1H-indol-3-yl)-2-isocyanopropanoic acid 1 in indolyl vinyl isocyanide biogenesis are reported. The characterization of iron/2-oxoglutarate (Fe/2OG) dependent desaturases IsnB and AmbI3 sheds light on the possible mechanism underlying stereoselective alkene installation to complete the biosynthesis of (E)- and (Z)-3-(2-isocyanovinyl)-1H-indole

  报道了新发现的异腈合酶（AmbI1和AmbI2）的体外重构以及在吲哚基乙烯基异氰酸酯生物发生中难以捉摸的中间体（S）-3-（1 H-吲哚-3-基）-2-异氰基丙酸1的检测。铁/ 2-氧戊二酸（Fe / 2OG）依赖的去饱和酶IsnB和AmbI3的表征揭示了立体选择性烯烃安装以完成（E）-和（Z）-3-（2-异氰基乙烯基）-的生物合成的可能机制。 1 H-吲哚2和5。易处理的异腈合酶系统（AmbI1和AmbI2）的建立为阐明神秘的异氰酸酯形成酶机制铺平了道路。
• Quantitative Analysis of <i>N</i>-Phenylpropenoyl-<scp>l</scp>-amino Acids in Roasted Coffee and Cocoa Powder by Means of a Stable Isotope Dilution Assay
  作者：Timo Stark、Helene Justus、Thomas Hofmann

  DOI：10.1021/jf053207q

  日期：2006.4.1

  N-phenylpropenoyl-L-amino acids as powerful antioxidants and key contributors to the astringent taste of cocoa nibs, there is an increasing interest in the concentrations of these phytochemicals in plant-derived foods. A versatile analytical method for the accurate quantitative analysis of N-phenylpropenoyl-L-amino acids in plant-derived foods by means of HPLC-MS/MS and synthetic stable isotope labeled N-phenylpropenoyl-L-amino

  自从最近有报道称N-苯基丙烯酰基-L-氨基酸作为强力抗氧化剂和可可豆粒涩味的主要贡献者以来，人们对植物性食品中这些植物化学物质的浓度越来越感兴趣。开发了一种通用的分析方法，该方法可通过HPLC-MS / MS和合成的稳定同位素标记的N-苯基丙烯酰基-L-氨基酸作为内标物，对植物衍生食品中的N-苯基丙烯酰基-L-氨基酸进行准确定量分析。通过开发的稳定同位素稀释法（SIDA），回收率达到95-102％，首次对可可和咖啡样品中的14种N-苯基丙烯酰基-L-氨基酸进行了定量。根据LC-MS / MS实验结果以及使用合成参考化合物N- [3'，4'进行共色谱法
• COMPOUNDS AND METHODS FOR THE TREATMENT OF PAIN AND OTHER DISEASES
  申请人：Sucholeiki Irving

  公开号：US20110257222A1

  公开（公告）日：2011-10-20

  The present invention relates generally to alkyne containing pharmaceutical agents, and in particular, to phenylethynyl-thiophene based metalloprotease inhibitor compounds. More particularly, the present invention provides a new class of MMP inhibiting compounds that exhibit increased potency, metabolic stability and/or reduced toxicity in relation to currently known MMP inhibitors for the treatment of pain and other diseases such as cancer. Additionally, the present invention relates to methods for treating pain in a patient comprising administering to the patient a pain-reducing effective amount of a present compound.

  本发明通常涉及含炔基的药物，特别是基于苯基乙炔基硫苯基的金属蛋白酶抑制剂化合物。更具体地说，本发明提供了一种新型MMP抑制剂化合物，其在治疗疼痛和其他疾病（如癌症）方面表现出增强的效力、代谢稳定性和/或降低的毒性，相对于目前已知的MMP抑制剂。此外，本发明还涉及治疗患者疼痛的方法，包括向患者施用一种当前化合物的减痛有效量。