D-Glu-γ-D-Glu | 4553-17-7

• 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: D-Glu-γ-D-Glu
• 英文别名: D-gamma-glutamyl-D-glutamic acid；(2R)-2-[[(4R)-4-amino-4-carboxybutanoyl]amino]pentanedioic acid
• CAS: 4553-17-7
• 化学式: C₁₀H₁₆N₂O₇
• 分子量: 276.246
• InChiKey: OWQDWQKWSLFFFR-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  167
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  Boc-D-Glu-OEt 在 甲醇 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 三氟乙酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 D-Glu-γ-D-Glu
  参考文献：
  名称：

  γ-Glutamyl-dipeptides: Easy tools to rapidly probe the stereoelectronic properties of the ionotropic glutamate receptor binding pocket

  摘要：

  gamma-Glutamyl-dipeptides, built by condensing the distal carboxylate of L-Glu (or D-Glu) onto a series of differently functionalized amino acids, were prepared and used as tools for rapidly probing the stereo electronic properties of iGluRs, searching for subtype-selective ligands. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.11.025

文献信息

• Anti-cancer compounds
  申请人：BRITISH TECHNOLOGY GROUP LIMITED

  公开号：EP0509643A1

  公开（公告）日：1992-10-21

  Quinazolines of the formula:- wherein R¹ is hydrogen or amino, or R¹ is alkyl, alkoxy or alkylthio each of up to 6 carbon atoms; or R¹ is aryl or aryloxy each of up to 10 carbon atoms; or R¹ is halogeno, hydroxy or mercapto; or R¹ is alkyl of up to 3 carbon atoms which bears one or more substituents selected from halogeno, hydroxy and alkanoylamino each of up to 6 carbon atoms; or R¹ is alkoxy of up to 3 carbon atoms which bears one or more substituents selected from hydroxy and alkoxy of up to 6 carbon atoms; wherein R² is hydrogen or alkyl, alkenyl, alkynyl, hydroxyalkyl, alkoxyalkyl, mercaptoalkyl, alkylthioalkyl, halogenoalkyl, cyanoalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkyanoylalkyl, carboxyalkyl, carbamoylalkyl or alkanoyl each of up to 6 carbon atoms; wherein Ar is phenylene or heterocyclene which is unsubstituted or which bears one or more substituents selected from halogeno, cyano, nitro, hydroxy, amino and carbomoyl and alkyl, alkoxy, halogenoalkyl, alkanoylamino, alkylthio and alkoxycarbonyl each of up to 6 carbon atoms; R³ is the residue of a dipeptide in which the first, N-terminal amino acid residue thereof attached to the carbonyl group of COR³ COR³ is an L- or D-amino acid residue -NHCH(C₂H)-A-CO- in which A is an alkylene group of up to 6 carbon atoms and the second amino acid residue is of an α-amino acid which has the D-configuration at its asymmetric α-carbon atom; wherein R⁴ is hydrogen or alkyl of up to 4 carbon atoms; wherein R⁵ is hydrogen or alkyl of up to 4 carbon atoms; and wherein each of R⁶, R⁷ and R⁸ is hydrogen or alkyl or alkoxy each of up to 4 carbon atoms; or is halogeno; or a pharmaceutically-acceptable salt, ester or amide thereof are of therapeutic value, particularly in the treatment of cancer.

  式中的喹唑啉类 其中 R¹ 是氢或氨基、 或 R¹ 是烷基、烷氧基或硫代烷基，每个最多 6 个碳原子； 或 R¹ 是芳基或芳氧基，每个最多 10 个碳原子； 或 R¹ 是卤素、羟基或巯基； 或 R¹是碳原子数不超过 3 个的烷基，带有一个或多个取代基，这些取代基可从卤素、羟基和烷酰氨基中选择，每个取代基的碳原子数不超过 6 个； 或 R¹ 是碳原子数不超过 3 个的烷氧基，带有一个或多个从羟基和碳原子数不超过 6 个的烷氧基中选出的取代基； 其中 R² 是氢或烷基、烯基、炔基、羟基烷基、烷氧基烷基、巯基烷基、烷硫基烷基、卤代烷基、氰基烷基、氨基烷基、烷基氨基烷基、二烷基氨基烷基、烷酰基烷基、羧基烷基、氨基甲酰基烷基或烷酰基，每个烷基最多 6 个碳原子； 其中 Ar 是未被取代的苯基或杂环基，或带有一个或多个取代基，这些取代基可选 自卤素、氰基、硝基、羟基、氨基和碳酰基以及烷基、烷氧基、卤代烷基、烷酰氨基、烷硫基 和烷氧羰基，每个取代基的碳原子数最多为 6 个； R³ 是二肽残基，其中与 COR³ COR³ 的羰基相连的第一个 N 端氨基酸残基是 L 或 D 氨基酸残基-NHCH(C₂H)-A-CO-，其中 A 是最多 6 个碳原子的亚烷基，第二个氨基酸残基是在α-碳原子上具有 D 构型的α-氨基酸； 其中 R⁴ 是氢或最多 4 个碳原子的烷基； 其中 R⁵ 是氢或最多 4 个碳原子的烷基；以及 其中R⁶、R⁷和R⁸各自为氢或烷基或烷氧基，每个最多4个碳原子；或卤素； 或其药学上可接受的盐、酯或酰胺具有治疗价值，特别是在治疗癌症方面。
• Microstructure of Poly(γ-glutamic acid) Produced by Bacillus subtilis Consisting of Clusters of <scp>d</scp>- and <scp>l</scp>-Glutamic Acid Repeating Units
  作者：Fei Wang、Masaji Ishiguro、Mai Mutsukado、Ken-ichi Fujita、Toshio Tanaka

  DOI：10.1021/jf8001262

  日期：2008.6.1

  Poly(gamma-glutamic acid) (PGA) produced by a strain of Bacillus subtilis was partially hydrolyzed into various oligopeptides so that the dipeptide fraction was isolated by the preparative thin-layer chromatography. HPLC analysis was applied to the detection of each of the four stereoisomers in this fraction using chemically synthesized authentic samples. The fraction consisted of N-gamma-D-glutamyl-D-glutamic acid, N-gamma-L-glutamyl-L-glutamic acid, N-gamma-D-glutamyl-L-glutamic acid, and N-gamma-L-glutamyl-D-glutamic acid at a ratio of 5.9:6.0: 1.0: 1.0. On the basis of this result, a model was proposed for the microstructure of the bacterial PGA, in which D- and L-glutamic acid repeating units are alternately linked in a single chain of the molecule.
• Williams; Thorne, Journal of Biological Chemistry, 1954, vol. 210, p. 203,206
  作者：Williams、Thorne

  DOI：——

  日期：——
• US5444061A
  申请人：——

  公开号：US5444061A

  公开（公告）日：1995-08-22
• [EN] ANTI-CANCER COMPOUNDS
  申请人：——

  公开号：WO1992016512A1

  公开（公告）日：1992-10-01

  [FR] On décrit des quinazolines de formule (I), dans laquelle R1 est hydrogène ou amino, ou R1 est alkyle, alcoxy ou alkylthio, chacun présentant jusqu'à 6 atomes de carbone; ou R1 est aryle ou aryloxy, chacun présentant jusqu'à 10 atomes de carbone; ou R1 est halogéno, hydroxy ou mercapto; où R1 est alkyle présentant jusqu'à 3 atomes de carbone, portant un ou plusieurs substituants choisis parmi halogéno, hydroxy et alcanoylamino, chacun présentant jusqu'à 6 atomes de carbone; ou R1 est alcoxy présentant jusqu'à 3 atomes de carbone, portant un ou plusieurs substituants choisis parmi hydroxy et alcoxy, présentant jusqu'à 6 atomes de carbone; dans laquelle R2 est hydrogène ou alkyle, alcényle, alcynyle, hydroxyalkyle, alcoxyalkyle, mercaptoalkyle, alkylthioalkyle, halogénoalkyle, cyanoalkyle, aminoalkyle, alkylaminoalkyle, dialkylaminoalkyle, alcanoylalkyle, carboxyalkyle, carbamoylalkyle ou alcanoyle, chacun présentant jusqu'à 6 atomes de carbone; dans laquelle Ar est phénylène ou hétérocyclène qui est non substitué ou qui porte un ou plusieurs substituants choisis parmi halogéno, cyano, nitro, hydroxy, amino et carbamoyle et alkyle, alcoxy, halogénoalkyle, alcanoylamino, alkylthio et alcoxycarbonyle, chacun présentant jusqu'à 6 atomes de carbone; R3 est le reste d'un dipeptide dans lequel le premier reste d'acide aminé N-terminal attaché au groupe carbonyle de COR3 est un reste d'acide aminé L ou D -NHCH(CO2H)-A-CO- dans lequel A est un groupe alkylène présentant jusqu'à 6 atomes de carbone et le deuxième reste d'acide aminé est d'un acide alpha-amino qui possède la configuration D au niveau de son atome alpha-carbone asymétrique; dans laquelle R4 est hydrogène ou alkyle présentant jusqu'à 4 atomes de carbone; dans laquelle R5 est hydrogène ou alkyle présentant jusqu'à 4 atomes de carbone; et dans laquelle chacun de R6, R7, R8 est hydrogène ou alkyle ou alcoxy, chacun présentant jusqu'à 4 atomes de carbone; ou est halogéno; ou un de leurs sels, esters ou amides pharmaceutiquement acceptables. Lesdites quinozalines
  [EN] Quinazolines of formula (I), wherein R?1 is hydrogen or amino, or R?1 is alkyl, alkoxy or alkylthio each of up to 6 carbon atoms; or R?1 is aryl or aryloxy each of up to 10 carbon atoms; or R?1 is halogeno, hydroxy or mercapto; or R?1 is alkyl of up to 3 carbon atoms which bears one or more substituents selected from halogeno, hydroxy and alkanoylamino each of up to 6 carbon atoms; or R?1 is alkoxy of up to 3 carbon atoms which bears one or more substituents selected from hydroxy and alkoxy of up to 6 carbon atoms; wherein R?2 is hydrogen or alkyl, alkenyl, alkynyl, hydroxyalkyl, alkoxyalkyl, mercaptoalkyl, alkylthioalkyl, halogenoalkyl, cyanoalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkanoylalkyl, carboxyalkyl, carbamoylalkyl or alkanoyl each of up to 6 carbon atoms; wherein Ar is phenylene or heterocyclene which is unsubstituted or which bears one or more substituents selected from halogeno, cyano, nitro, hydroxy, amino and carbamoyl and alkyl, alkoxy, halogenoalkyl, alkanoylamino, alkylthio and alkoxycarbonyl each of up tp 6 carbon atoms;R?3 is the residue of a dipeptide in which the first, N-terminal amino acid residue thereof attached to the carbonyl group of COR?3 is an L- or D-amino acid residue -NHCH(CO2?H)-A-CO- in which A is an alkylene group of up to 6 carbon atoms and the second amino acid residue is of an $g(a)-amino acid which has the D-configuration at its asymmetric $g(a)-carbon atom; wherein R?4 is hydrogen or alkyl of up to 4 carbon atoms; wherein R?5 is hydrogen or alkyl of up to 4 carbon atoms; and wherein each of R?6, R?7 and R?8 is hydrogen or alkyl or alkoxy each of up to 4 carbon atoms; or is halogeno; or a pharmaceutically-acceptable salt, ester or amide thereof are of therapeutic value, particularly in the treatment of cancer.