L-Glu-(D-Trp)-OH

• 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: L-Glu-(D-Trp)-OH
• 英文别名: γ-L-glutamyl-D-tryptophan；(2S)-2-amino-5-[[(1R)-1-carboxy-2-(1H-indol-3-yl)ethyl]amino]-5-oxopentanoic acid
• 化学式: C₁₆H₁₉N₃O₅
• 分子量: 333.344
• InChiKey: CATMPQFFVNKDEY-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-benzyloxycarbonyl-γ-L-glutamyl-D-tryptophan α-benzyl ester 在 palladium-carbon 作用下， 以 甲醇 为溶剂， 生成 L-Glu-(D-Trp)-OH
  参考文献：
  名称：

  .gamma.-glutamyl and .beta.-aspartyl containing immunomodulator

  摘要：

  提供具有γ-L-谷氨酰基，γ-D-谷氨酰基，β-L-天冬氨酰基或β-D-天冬氨酰基官能团的合成免疫调节分子，如公式A所示。在公式A中，“n”为1或2，R为氢，酰基或烷基，X为芳香族或杂环氨基酸或其衍生物。一个特别优选的实施例是γ-D-谷氨酰基-L-色氨酸，具有免疫调节活性。

  公开号：

  US05916878A1

文献信息

• [EN] PRODRUGS OF D-GAMMA-GLUTAMYL-D-TRYPTOPHAN AND D-GAMMA- GLUTAMYL-L-TRYPTOPHAN<br/>[FR] PROMÉDICAMENTS DE D-GAMMA-GLUTAMYL-D-TRYPTOPHANE ET D-GAMMA-GLUTAMYL-L-TRYPTOPHANE
  申请人：APOTEX TECHNOLOGIES INC

  公开号：WO2012129680A1

  公开（公告）日：2012-10-04

  The present invention provides pro-drugs of D-gamma-glutamyl-[D/L] -tryptophan, said pro-drugs are compounds of Formula I or pharmaceutically acceptable salts thereof, wherein G is C1-C8 alkyl or benzyl, T is C1-C8 alkyl or benzyl, and * is a chiral carbon in a (R) or (S) configuration, provided that when * is in the (R) configuration, at least one of G and T is C5-C8 alkyl; and use of compounds of Formula I in a pharmaceutical composition.

  本发明提供D-γ-谷氨酰-[D/L]-色氨酸的前药，所述前药是化合物I的药用可接受盐，其中G为C1-C8烷基或苄基，T为C1-C8烷基或苄基，*为(R)或(S)构型的手性碳，但当*为(R)构型时，至少有一个G和T为C5-C8烷基；以及化合物I在制药组合物中的使用。
• CRYSTALLINE D-ISOGLUTAMYL-D-TRYPTOPHAN AND THE MONO AMMONIUM SALT OF D-ISOGLUTAMYL-D-TRYPTOPHAN
  申请人：Tam Tim Fat

  公开号：US20100016243A1

  公开（公告）日：2010-01-21

  A process for making pure crystalline D-isoglutamyl-D-tryptophan is provided which includes the step of deprotecting essentially pure N-tert-butoxycarbonyl-D-isoglutamyl-D-tryptophan or its diester to yield essentially pure D-isoglutamyl-D-tryptophan. A process is also provided for the preparation of pure mono ammonium salt of D-isoglutamyl-D-tryptophan from essentially pure N-tert-butoxycarbonyl-D-isoglutamyl-D-tryptophan. D-isoglutamyl-D-tryptophan, ammonium salt (1:1) is a stable pharmaceutical solid.

  提供了一种制备纯结晶D-异戊氨酰-D-色氨酸的过程，包括去保护基本纯的N-叔丁氧羰基-D-异戊氨酰-D-色氨酸或其二酯的步骤，以得到基本纯的D-异戊氨酰-D-色氨酸。还提供了一种从基本纯的N-叔丁氧羰基-D-异戊氨酰-D-色氨酸制备纯D-异戊氨酰-D-色氨酸单铵盐的过程。D-异戊氨酰-D-色氨酸，铵盐（1:1）是一种稳定的药用固体。
• TEMPLATE-FIXED PEPTIDOMIMETICS WITH CCR10 ANTAGONISTIC ACTIVITY
  申请人：Jung Francoise

  公开号：US20120283168A1

  公开（公告）日：2012-11-08

  Novel template-fixed β-hairpin peptidomimetics of the general formula (I) wherein the single elements T or P are α-amino acid residues connected in either direction which, depending on their positions in the chain, are as defined in the description and the claims, and salts thereof, have the property to antagonize the receptor CCR10. They can be used as medicaments to treat or prevent diseases or conditions in the area of dermatological and cutaneous disorders, inflammation, allergic disorders, respiratory diseases, diseases of the gastro-intestinal tract, ophthalmic diseases, haematology and cancer. These β-hairpin peptidomimetics can be manufactured by a process which is based on a mixed solid- and solution phase synthetic strategy.

  具有以下一般式(I)的小说模板固定β-发夹仿生肽，其中单个元素T或P是α-氨基酸残基，可以连接在任何方向上，具体取决于它们在链中的位置，如描述和索赔中所定义，及其盐，具有拮抗受体CCR10的特性。它们可用作药物，用于治疗或预防皮肤病和皮肤疾病、炎症、过敏性疾病、呼吸道疾病、胃肠道疾病、眼科疾病、血液学和癌症等领域。这些β-发夹仿生肽可以通过基于混合固相和溶液相合成策略的过程制备。
• ORALLY BIOAVAILABLE D-GAMMA-GLUTAMYL-D-TRYPTOPHAN
  申请人：TAM Tim Fat

  公开号：US20120157387A1

  公开（公告）日：2012-06-21

  Provided are compounds which are prodrugs of D-gamma-glutamyl-D-tryptophan, methods of making the compounds and methods for using the compounds.

  提供的是D-γ-谷氨酰-D-色氨酸的前药化合物，制备这些化合物的方法以及使用这些化合物的方法。
• CRYSTALLINE D-ISOGLUTAMYL-D-TRYPTOPHAN AND THE MONO AMMONIUM SLAT OF D-ISOGLUTAMYL-D-TRYPTOPHAN
  申请人：TAM Tim Fat

  公开号：US20130059791A1

  公开（公告）日：2013-03-07

  A process for making pure crystalline D-isoglutamyl-D-tryptophan is provided which includes the step of deprotecting essentially pure N-tert-butoxycarbonyl-D-isoglutamyl-D-tryptophan or its diester to yield essentially pure D-isoglutamyl-D-tryptophan. A process is also provided for the preparation of pure mono ammonium salt of D-isoglutamyl-D-tryptophan from essentially pure N-tert-butoxycarbonyl-D-isoglutamyl-D-tryptophan. D-isoglutamyl-D-tryptophan, ammonium salt (1:1) is a stable pharmaceutical solid.

  提供了一种制备纯结晶D-异谷氨酰-D-色氨酸的过程，包括去保护基的步骤，将基本上纯的N-叔丁氧羰基-D-异谷氨酰-D-色氨酸或其二酯去保护，得到基本上纯的D-异谷氨酰-D-色氨酸。还提供了一种从基本上纯的N-叔丁氧羰基-D-异谷氨酰-D-色氨酸制备纯D-异谷氨酰-D-色氨酸单酰胺盐的过程。D-异谷氨酰-D-色氨酸铵盐（1:1）是一种稳定的药物固体。