Fmoc-L-Val-benzotriazol-1-yl ester | 1126433-37-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-L-Val-benzotriazol-1-yl ester
• 英文别名: Fmoc-L-Val-Bt；N-Fmoc-L-Val-Bt；Fmoc-Val-Bt；9H-fluoren-9-ylmethyl N-[(2S)-1-(benzotriazol-1-yl)-3-methyl-1-oxobutan-2-yl]carbamate
• CAS: 1126433-37-1
• 化学式: C₂₆H₂₄N₄O₃
• 分子量: 440.502
• InChiKey: BXOWZCNNYZYNLS-DEOSSOPVSA-N

物化性质

• 熔点：
  151.9-152.6 °C
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  86.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Fmoc-L-Val-benzotriazol-1-yl ester 、 Fmoc-L-苯丙氨酸 以100%的产率得到Fmoc-L-Val-L-Phe-OH
  参考文献：
  名称：

  A protocol for racemization-free loading of Fmoc-amino acids to Wang resin

  摘要：

  Fmoc-amino acids are conveniently and inexpensively linked to Wang resin using benzyloxybenzyl chloride resin without the problems normally associated with the traditional methods of preparation of Fmoc-amino acid loaded Wang resins, namely, low substitution, unacceptable racemization or use of expensive reagents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.055
• 作为产物：
  描述：

  T406石油添加剂 、 (S)-(9H-芴-9-基)甲基(1-氯-3-甲基-1-氧代-2-丁基)氨基甲酸酯 以 四氢呋喃 为溶剂， 生成 Fmoc-L-Val-benzotriazol-1-yl ester
  参考文献：
  名称：

  Benzotriazole-Assisted Solid-Phase Assembly of Leu-Enkephalin, Amyloid β segment 34−42, and other “Difficult” Peptide Sequences

  摘要：

  Microwave-assisted solid-phase syntheses of six "difficult" peptides, H-VVSVV-NH(2) (3), H-VVVSVV-NH(2) (4), H-VIVIG-OH (5), H-TVTVTV-NH(2) (6), H-VKDGYI-NH(2) (7), and H-VKDVYI-NH(2) (8), were achieved utilizing N-(Fmoc-(alpha-aminoacyl)benzotriazoles. Extension to the syntheses of Leu-enkephalin (9) and amyloid-beta (34-42) (10) demonstrates that this strategy comprises an efficient route to new and known "difficult" peptides.

  DOI：

  10.1021/jo8026214

文献信息

• An efficient method for the preparation of peptide alcohols
  作者：Alan Roy Katritzky、Nader Elmaghwry Abo-Dya、Srinivasa Rao Tala、Kapil Gyanda、Zakaria Kamel Abdel-Samii

  DOI：10.1039/b905730g

  日期：——

  N -Protected LL-dipeptide alcohols 3a–p, diastereomeric mixture (3d + 3d′) and tripeptide alcohols 6a–c were synthesized by treatment of various amino alcohols with N-protected(α-aminoacyl)benzotriazoles 1a–c, 1f–m, (1a + 1a′) and N-protected(α-dipeptidoyl)benzotriazoles 5a, 5b respectively in good yields with complete retention of chirality.

  氮 -通过用N-保护的(α-氨基酰基)苯并三唑1a-c、1f-m处理各种氨基醇合成受保护的LL-二肽醇3a-p、非对映体混合物(3d + 3d')和三肽醇6a-c， (1a + 1a') 和 N-保护的(α-二肽酰基)苯并三唑 5a、5b 分别具有良好的产率，并且完全保留了手性。
• Efficient and Selective Syntheses of S-Acyl and N-Acyl Glutathiones
  作者：Alan Katritzky、Nader Abo- Dya、Srinivasa Tala、Ebrahim Ghazvini-Zadeh、Kiran Bajaj、Said El-Feky

  DOI：10.1055/s-0029-1219837

  日期：2010.6

  Selective syntheses of S-acyl glutathiones are achieved in 79-98% yields using 1-acyl-1H-benzotriazoles in the presence of potassium bicarbonate in aqueous methanol at 20 ˚C. N-Acylation of S-(p-nitrobenzoyl) glutathione with 1-acyl-1H-benzotriazoles followed by deprotection of the p-nitrobenzoyl groups under mild conditions gave 63-78% yields of N-acyl glutathiones. These methodologies should be useful for the S-acylation and N-acylation of peptides and glycopeptides.

  在 20 ËC 的甲醇水溶液中，在碳酸氢钾存在下，使用 1-酰基-1H-苯并三唑选择性合成 S-酰基谷胱甘肽，产率为 79-98%。用 1-酰基-1H-苯并三唑对 S-（对硝基苯甲酰基）谷胱甘肽进行 N-酰化，然后在温和的条件下对对硝基苯甲酰基进行脱保护，可得到产率为 63-78% 的 N-酰基谷胱甘肽。这些方法可用于肽和糖肽的 S-酰化和 N-酰化。
• Benzotriazole-Assisted Solid-Phase Assembly of Leu-Enkephalin, Amyloid β segment 34−42, and other “Difficult” Peptide Sequences
  作者：Alan R. Katritzky、Danniebelle N. Haase、Jodie V. Johnson、Alfred Chung

  DOI：10.1021/jo8026214

  日期：2009.3.6

  Microwave-assisted solid-phase syntheses of six "difficult" peptides, H-VVSVV-NH(2) (3), H-VVVSVV-NH(2) (4), H-VIVIG-OH (5), H-TVTVTV-NH(2) (6), H-VKDGYI-NH(2) (7), and H-VKDVYI-NH(2) (8), were achieved utilizing N-(Fmoc-(alpha-aminoacyl)benzotriazoles. Extension to the syntheses of Leu-enkephalin (9) and amyloid-beta (34-42) (10) demonstrates that this strategy comprises an efficient route to new and known "difficult" peptides.
• A protocol for racemization-free loading of Fmoc-amino acids to Wang resin
  作者：Krishnarao Sandhya、Bhagavathula Ravindranath

  DOI：10.1016/j.tetlet.2008.02.055

  日期：2008.4

  Fmoc-amino acids are conveniently and inexpensively linked to Wang resin using benzyloxybenzyl chloride resin without the problems normally associated with the traditional methods of preparation of Fmoc-amino acid loaded Wang resins, namely, low substitution, unacceptable racemization or use of expensive reagents. (C) 2008 Elsevier Ltd. All rights reserved.