N-allyloxycarbonyl α-allyl-L-glutamate | 91871-28-2

• 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
• 英文名称: N-allyloxycarbonyl α-allyl-L-glutamate
• 英文别名: Alloc-Glu-OAllyl；(4S)-5-oxo-5-prop-2-enoxy-4-(prop-2-enoxycarbonylamino)pentanoic acid
• CAS: 91871-28-2
• 化学式: C₁₂H₁₇NO₆
• 分子量: 271.27
• InChiKey: FIQWQKADKBCOOJ-VIFPVBQESA-N

物化性质

• 沸点：
  449.5±45.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-allyloxycarbonyl α-allyl-L-glutamate 在 四(三苯基膦)钯 二乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以100%的产率得到L-谷氨酸
  参考文献：
  名称：

  Efficient Syntheses of Pyrofolic Acid and Pteroyl Azide, Reagents for the Production of Carboxyl-Differentiated Derivatives of Folic Acid

  摘要：

  Reaction of folic acid (1) with excess trifluoroacetic anhydride provides access to both the previously unknown N-10-(trifluoroacetyl)pyrofolic acid (8) and pyrofolic acid (9). Reaction of either of these materials with hydrazine selectively affords pteroyl hydrazide (13), which may be oxidized to pteroyl azide (27) on a large scale (62% overall from 1 without the need for chromatography). Treatment of 27 with differentially protected glutamates provides a convenient and high-yielding synthesis of differentially protected, optically pure folates.

  DOI：

  10.1021/ja971568j
• 作为产物：
  描述：

  Fmoc-O-叔丁基-L-谷氨酸 在 sodium carbonate 、 caesium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 二乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 25.17h， 生成 N-allyloxycarbonyl α-allyl-L-glutamate
  参考文献：
  名称：

  A new class of NO-donor pro-drugs triggered by γ-glutamyl transpeptidase with potential for reno-selective vasodilatation

  摘要：

  这篇通讯描述了一种新型 N-羟基胍（NHG）原药的合成过程，这种原药在δ-谷氨酰转肽酶（δ-GT）的作用下释放一氧化氮（NO），具有治疗急性肾损伤/衰竭（ARI/ARF）的潜力。

  DOI：

  10.1039/c2cc38382a

文献信息

• Diaminodiacid-Based Solid-Phase Synthesis of Peptide Disulfide Bond Mimics
  作者：Hong-Kui Cui、Ye Guo、Yao He、Feng-Liang Wang、Hao-Nan Chang、Yu-Jia Wang、Fang-Ming Wu、Chang-Lin Tian、Lei Liu

  DOI：10.1002/anie.201302197

  日期：2013.9.2

  The antimicrobial peptide tachyplesin I was used as a model to apply the title strategy, which was developed for the preparation of peptidic macrocycles with double disulfide surrogates. The folding and activity of the tachyplesin I analogues were found to be sensitive to the structure of the disulfide surrogates, thus underlining the necessity of a flexible synthetic route for generating disulfide

  抗菌肽速激肽I被用作应用标题策略的模型，该策略是为制备具有双二硫化物替代物的肽大环化合物而开发的。发现速激肽I类似物的折叠和活性对二硫化物替代物的结构敏感，因此强调了需要灵活的合成路线来产生具有高结构多样性的二硫键替代物。
• PRODRUG-TYPE ANTICANCER AGENT USING CANCER-SPECIFIC ENZYMATIC ACTIVITY
  申请人：The University of Tokyo

  公开号：US20200399305A1

  公开（公告）日：2020-12-24

  To provide novel compounds that are promising as prodrug-type anticancer agents, a compound represented by general formula (I) or a salt thereof is provided.

  提供具有前瞻性作为前药型抗癌药物的新化合物，提供了一种由通用式(I)表示的化合物或其盐。
• Asymmetric bismuth-rhodamines as an activatable fluorogenic photosensitizer
  作者：Akari Mukaimine、Tasuku Hirayama、Hideko Nagasawa

  DOI：10.1039/d0ob02456b

  日期：——

  can be cleaved by γ-glutamyl transpeptidase (GGT) to produce BiRNH, which acts as a red-light-excitable fluorophore and photosensitizer. A cell study revealed that the phototoxicity and fluorescence of BiRGlu could be simultaneously and selectively activated in the cells with high GGT activity. Thus, we established that BiRNH could be envisaged as a versatile scaffold for activatable fluorogenic photosensitizers

  铋-罗丹明化合物因其独特的可激发光敏特性和伴随的荧光而脱颖而出；然而，需要进一步了解结构-性能关系以扩大其实际应用范围。为此，本研究描述了第一个不对称掺入铋的罗丹明、BiRNH和BiRAc的例子，包括它们的合成、光物理性质和光敏能力。在红光激发下，BiRNH表现出可检测的发射和光敏特性，而N-乙酰化衍生物BiRAc显示出吸收波长的深移以及发射和光敏能力的衰减。这些显着不同的光物理特性使我们能够设计一种可激活的荧光光敏剂BiRGlu，它带有一个 γ-谷氨酰基而不是BiRAc中的乙酰基。γ-谷氨酰基团可以被 γ-谷氨酰转肽酶 (GGT) 裂解产生BiRNH，它作为红光可激发荧光团和光敏剂。一项细胞研究表明，BiRGlu的光毒性和荧光可以在具有高 GGT 活性的细胞中同时选择性地激活。因此，我们确定了BiRNH可以设想为可激活荧光光敏剂的多功能支架。
• Synthesis and Evaluation of Taxol–Folic Acid Conjugates as Targeted Antineoplastics † †See ref 1.
  作者：Jae Wook Lee、June Y Lu、P.S Low、P.L Fuchs

  DOI：10.1016/s0968-0896(02)00019-6

  日期：2002.7

  A series of Taxol derivatives tethered at C2' and C-7 to glutamate and folate have been synthesized for evaluation as prodrugs which release Taxol via hydrolytic lability of their alpha-alkoxy and alpha-amino esters. The half-time for hydrolysis of these materials was determined in pH 7 and pH 5 buffer. The in vitro cytotoxicity has been assessed in cell culture against A-549 lung cancer, MCF-7 breast cancer, and HT-29 colon cancer. Selected agents were further screened for folate binding and competitive binding with free folic acid, One agent (54), further evaluated in animal Studies as found to increase the lifespan in mice, but was less effective than Taxol itself. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Reduction of Azides to Primary Amines in Substrates Bearing Labile Ester Functionality. Synthesis of a PEG-Solubilized, “Y”-Shaped Iminodiacetic Acid Reagent for Preparation of Folate-Tethered Drugs¹
  作者：Jae Wook Lee、Philip L. Fuchs

  DOI：10.1021/ol9905248

  日期：1999.7.1

  Anhydride 3 is a useful reagent for the synthesis of triply linked drug conjugates. Examples using paclitaxel are provided. Conversion of the azido moiety to a primary amine in the presence of substrates bearing labile ester functionality requires the use of a tin/mercaptan reducing system which includes methanol exchange equilibration to effect nitrogen-tin bond scission.