Fmoc-Asp(OBn)-Ala-OH | 169393-80-0

• 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: Fmoc-Asp(OBn)-Ala-OH
• 英文别名: (2S)-2-[(2S)-3-(benzyl carboxy)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanamido]propanoic acid；(2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxo-4-phenylmethoxybutanoyl]amino]propanoic acid
• CAS: 169393-80-0
• 化学式: C₂₉H₂₈N₂O₇
• 分子量: 516.551
• InChiKey: GWUMAOZCGWLOKS-BVZFJXPGSA-N

物化性质

• 熔点：
  148-149 °C
• 沸点：
  803.8±65.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Fmoc-Asp(OBn)-Ala-OH 在 哌啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 生成 H-Asp(OBn)-Ala-Asp(OBn)-Asp(OBn)-OBn
  参考文献：
  名称：

  Carbonic anhydrase activators: Human isozyme II is strongly activated by oligopeptides incorporating the carboxyterminal sequence of the bicarbonate anion exchanger AE1

  摘要：

  Di-/tri- and especially tetrapeptides incorporating the sequence DADD present in the carboxyterminal region of the bicarbonate, chloride anion exchanger AE1 strongly activate human carbonic anhydrase (CA) isozyme II, whereas they act as more inefficient activators of isozymes I and IV. This discovery suggests that in the metabolon hCA II-AE1. the last protein plans a role both as a CA activator as well as a bicarbonate transporter. A synthesis of the tripeptide DAD and the tetrapeptide DADD is also presented together with the possible explanation why such highly acidic oligopeptides efficiently bind to hCA II but not to the closely related isozymes I and IV. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00121-x
• 作为产物：
  描述：

  芴甲氧羰基-天冬氨酸-β苄脂 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 生成 Fmoc-Asp(OBn)-Ala-OH
  参考文献：
  名称：

  Carbonic anhydrase activators: Human isozyme II is strongly activated by oligopeptides incorporating the carboxyterminal sequence of the bicarbonate anion exchanger AE1

  摘要：

  Di-/tri- and especially tetrapeptides incorporating the sequence DADD present in the carboxyterminal region of the bicarbonate, chloride anion exchanger AE1 strongly activate human carbonic anhydrase (CA) isozyme II, whereas they act as more inefficient activators of isozymes I and IV. This discovery suggests that in the metabolon hCA II-AE1. the last protein plans a role both as a CA activator as well as a bicarbonate transporter. A synthesis of the tripeptide DAD and the tetrapeptide DADD is also presented together with the possible explanation why such highly acidic oligopeptides efficiently bind to hCA II but not to the closely related isozymes I and IV. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00121-x

文献信息

• An expedient route for the reduction of carboxylic acids to alcohols employing 1-propanephosphonic acid cyclic anhydride as acid activator
  作者：G. Nagendra、C. Madhu、T.M. Vishwanatha、Vommina V. Sureshbabu

  DOI：10.1016/j.tetlet.2012.06.108

  日期：2012.9

  method for the synthesis of alcohols from the corresponding carboxylic acids is described. Activation of carboxylic acid with 1-propanephosphonic acid cyclic anhydride (T3P) and subsequent reduction using NaBH4 yield the alcohol in excellent yields with good purity. Reduction of several alkyl/aryl carboxylic acids and Nα-protected amino acids/peptide acids as well as Nβ-protected amino acids was successfully

  描述了一种由相应的羧酸合成醇的简单有效的方法。用1-丙烷膦酸环酐（T3P）活化羧酸，然后使用NaBH 4还原，可得到纯度高，纯度高的醇。的减少几个烷基/芳基羧酸和N α -保护的氨基酸/肽酸以及如N β -保护的氨基酸被成功地执行，以获得良好的收率相应的醇。所有产物均通过1 H NMR和质谱分析充分表征。该过程温和，简单，并且容易分离产物。
• HOBt·DCHA-Mediated Synthesis of Sterically Hindered Peptides employing Fmoc-Amino Acid Chlorides in Both Solution-Phase and Solid Phase Methods
  作者：Vommina V. Sureshbabu、Naremaddepalli S. Sudarshan、G. Chenna Krishna

  DOI：10.1080/00397910802219536

  日期：2008.7.24

  Abstract The synthesis of peptides employing Fmoc-amino acid chlorides in presence of HOBt·DCHA salt in solution as well as by the solid-phase methods is described. The coupling was found to be complete in 30 min and free from racemization. The synthesis of β-casomorphin by solid-phase protocol employing Fmoc-amino acid chloride/HOBt·DCHA in DMF–CH2Cl2 has also been outlined. The final peptide was

  摘要 描述了在溶液中存在 HOBt·DCHA 盐的情况下使用 Fmoc-氨基酸氯化物以及固相方法合成肽。发现偶联在 30 分钟内完成并且没有外消旋。还概述了使用 Fmoc-氨基酸氯化物/HOBt·DCHA 在 DMF-CH2Cl2 中通过固相方案合成 β-酪啡肽。最终的肽以 80% 的产率获得并被充分表征。
• Surcshbabu, Vommina V.; Sudarshan; Chennakrishnareddy, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 4, p. 574 - 579
  作者：Surcshbabu, Vommina V.、Sudarshan、Chennakrishnareddy

  DOI：——

  日期：——
• Babu, Vommina V. Suresh; Kantharaju; Sudarshan, Naremaddepalli S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 8, p. 1880 - 1886
  作者：Babu, Vommina V. Suresh、Kantharaju、Sudarshan, Naremaddepalli S.

  DOI：——

  日期：——
• Carbonic anhydrase activators: Human isozyme II is strongly activated by oligopeptides incorporating the carboxyterminal sequence of the bicarbonate anion exchanger AE1
  作者：Andrea Scozzafava、Claudiu T Supuran

  DOI：10.1016/s0960-894x(02)00121-x

  日期：2002.4

  Di-/tri- and especially tetrapeptides incorporating the sequence DADD present in the carboxyterminal region of the bicarbonate, chloride anion exchanger AE1 strongly activate human carbonic anhydrase (CA) isozyme II, whereas they act as more inefficient activators of isozymes I and IV. This discovery suggests that in the metabolon hCA II-AE1. the last protein plans a role both as a CA activator as well as a bicarbonate transporter. A synthesis of the tripeptide DAD and the tetrapeptide DADD is also presented together with the possible explanation why such highly acidic oligopeptides efficiently bind to hCA II but not to the closely related isozymes I and IV. (C) 2002 Elsevier Science Ltd. All rights reserved.