色氨酰-脯氨酸 | 38136-75-3

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 脯氨酸类衍生物
• 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
• 中文名称: 色氨酰-脯氨酸
• 英文名称: Trp-Pro
• 英文别名: (2S)-1-[(2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoyl]pyrrolidine-2-carboxylate
• CAS: 38136-75-3
• 化学式: C₁₆H₁₉N₃O₃
• 分子量: 301.345
• InChiKey: DXYQIGZZWYBXSD-JSGCOSHPSA-N

物化性质

• 沸点：
  626.4±55.0 °C(Predicted)
• 密度：
  1.388±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  99.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  色氨酰-脯氨酸 在 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成
  参考文献：
  名称：

  含色氨酸的肽的铜催化位点选择性C（sp2）-H自由基三氟甲基化。

  摘要：

  肽框架内CH键的位点选择性功能化是最重要的合成相关挑战。在这里，我们报告含有色氨酸（Trp）的肽的操作简单C（sp2）-H三氟甲基化。该氟化技术的特征在于其手性保留，官能团的耐受性和可扩展性，并且相对于其他氨基酸和杂环单元，对Trp残基表现出化学选择性。结果，它代表了后期肽修饰和蛋白质工程的可持续工具。

  DOI：

  10.1021/acs.orglett.0c00033
• 作为产物：
  描述：

  Fmoc-Trp-Pro-OH 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 色氨酰-脯氨酸
  参考文献：
  名称：

  Functional Identification and Structure Determination of Two Novel Prolidases from cog1228 in the Amidohydrolase Superfamily,

  摘要：

  Two uncharacterized enzymes from the amidohydrolase superfamily belonging to cog1228 were cloned, expressed, and purified to homogeneity. The two proteins, Sgx9260c (gi|44242006) and Sgx9260b (gi|44479596), were derived from environmental DNA samples originating from the Sargasso Sea. The catalytic function and substrate profiles for Sgx9260c and Sgx9260b were determined using a comprehensive library of dipeptides and N-acyl derivative of L-amino acids. Sgx9260c catalyzes the hydrolysis of Gly-L-Pro, L-Ala-L-Pro, and N-acyl derivatives of L-Pro. The best substrate identified to date is N-acetyl-L-Pro with a value of k(cat)/K-m of 3 x 10(5) M-1 s(-1). Sgx9260b catalyzes the hydrolysis of L-hydrophobic L-Pro dipeptides and N-acyl derivatives of L-Pro. The best substrate identified to date is N-propionyl-L-Pro with a value of k(cat)/K-m of 1 x 10(5) M-1 s(-1). Three-dimensional structures of both proteins were determined by X-ray diffraction methods (PDB codes 3MKV and 3FEQ). These proteins fold as distorted (beta/alpha)(8)-barrels with two divalent cations in the active site. The structure of Sgx9260c was also determined as a complex with the N-methylphosphonate derivative of L-Pro (PDB code 3N2C). In this structure the phosphonate moiety bridges the binuclear metal center, and one oxygen atom interacts with His-140. The a-carboxylate of the inhibitor interacts with Tyr-231. The proline side chain occupies a small substrate binding cavity formed by residues contributed from the loop that follows beta-strand 7 within the (beta/alpha)(8)-barrel. A total of 38 other proteins from cog1228 are predicted to have the same substrate profile based on conservation of the substrate binding residues. The structure of an evolutionarily related protein, Cc2672 from Caulobacter crecentus, was determined as a complex with the N-methylphosphonate derivative of L-arginine (PDB code 3MTW).

  DOI：

  10.1021/bi100897u

文献信息

• Novel Fluorogenic substrates containing Bimane system for microdetermination of angiotensin I converting enzyme.
  作者：Eisuke SATO、Satoko NISHIKAWA、Yuichi KANAOKA

  DOI：10.1248/cpb.37.145

  日期：——

  As a sensitive fluorometric assay for the activity of angiotensin converting enzyme, bimane-peptides containing tryptophan, i.e., 1, 7-dioxo-2, 5, 6-trimethyl-1H, 7H, pyrazolo[1, 2-α]pyrazol-3-yl-methylthiomethylcarbonyl-glycyl (or L-phenylalanyl)-L-tryptophyl-L-leucine (or L-proline), were synthesized and shown to be potent fluorogenic substrates for the micro-determination of angiotensin I converting enzyme activity.

  作为一种灵敏的荧光分析法，用于检测血管紧张素转化酶活性的含吲哚乙酸的联苯胺肽，即1, 7-二氧-2, 5, 6-三甲基-1H, 7H, 吡唑[1, 2-α]吡唑-3-基-甲硫甲酰基-甘氨酰(或L-苯丙氨酰)-L-色氨酰-L-亮氨酸(或L-脯氨酸)，已被合成，并被证明是用于微量测定血管紧张素I转化酶活性的强效荧光底物。
• Processes for preparing eptifibatide and pertinent intermediate compounds
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：EP2204383A1

  公开（公告）日：2010-07-07

  The present invention provides, inter alia, convergent processes for preparing eptifibatide that involve coupling a 2-6 eptifibatide fragment to an activated cysteinamide residue to form a 2-7 eptifibatide fragment, attaching a mercaptopropionic acid residue to the 2-7 eptifibatide fragment through disulfide bond formation, coupling the peptide intramolecularly, and removing the protecting group, to form eptifibatide. The invention further provides products produced by the described processes, novel compounds that can be used as synthetic intermediates for the preparation of eptifibatide, and novel compounds that are structurally similar to eptifibatide.

  本发明提供了制备依普利贝肽的汇聚过程，其中涉及将2-6依普利贝肽片段与活性半胱氨酰残基偶联形成2-7依普利贝肽片段，通过二硫键形成将巯基丙酸残基连接到2-7依普利贝肽片段上，将肽链分子内耦合，去除保护基，形成依普利贝肽。本发明进一步提供了通过上述过程制备的产品、可用作依普利贝肽合成中间体的新化合物以及结构类似于依普利贝肽的新化合物。
• Peptide manufacturing process
  申请人：Callens Roland

  公开号：US20110092671A1

  公开（公告）日：2011-04-21

  A process for the manufacture of peptide Omiganan in solution phase. Novel intermediates in the process for the manufacture of Omiganan and processes for the manufacture of these intermediates.

  一种在溶液相中制造肽Omiganan的工艺。该工艺中的新型中间体，以及制造这些中间体的工艺。
• Nutrient compositions containing peptides
  申请人：CLINTEC NUTRITION COMPANY

  公开号：EP0457314A1

  公开（公告）日：1991-11-21

  Nutrient compositions comprise an aqueous solution of at least one dipeptide with an N-terminal amino acid selected from glutamine, aspargine, tyrosine, tryptophan, and aspargine. The C-terminal amino acid is alanine, glycine, tryptophan, arginine, proline or serine. The nutritional compositions contain from about 0.1 to 25.0 percent by weight of oligopeptides, preferably about 0.5 to 5.0 percent by weight.

  营养组合物包含至少一种二肽的水溶液，其 N 端氨基酸选自谷氨酰胺、天门冬氨酸、酪氨酸、色氨酸和天门冬氨酸。 C 端氨基酸为丙氨酸、甘氨酸、色氨酸、精氨酸、脯氨酸或丝氨酸。营养组合物含有约 0.1%至 25.0%（按重量计）的低聚肽，最好是约 0.5%至 5.0%（按重量计）。
• ADDITIVE FOR UNDIFFERENTIATION MAINTAINING MEDIUM
  申请人：Ajinomoto Co., Inc.

  公开号：EP3604503A1

  公开（公告）日：2020-02-05

  The present invention provides a medium for culturing pluripotency stem cells, containing L-tryptophan or L-tryptophan derivative at a concentration of not less than 176 µM.

  本发明提供了一种培养多能干细胞的培养基，其中含有浓度不低于 176 µM 的 L-色氨酸或 L-色氨酸衍生物。