Boc-Asp-OAll | 88224-27-5

• 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: Boc-Asp-OAll
• 英文别名: (3S)-3-{[(tert-butoxy)carbonyl]amino}-4-oxo-4-(prop-2-en-1-yloxy)butanoic acid；(3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-prop-2-enoxybutanoic acid
• CAS: 88224-27-5
• 化学式: C₁₂H₁₉NO₆
• 分子量: 273.286
• InChiKey: IAEZDRCCBIEBCS-QMMMGPOBSA-N

物化性质

• 沸点：
  437.6±45.0 °C(Predicted)
• 密度：
  1.175±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：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  Boc-Asp-OAll 在 N-甲基吗啉 、 咪唑 、 sodium tetrahydroborate 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.25h， 生成 allyl (S)-2-(tert-butyloxycarbonyl)amino-4-iodobutanoate
  参考文献：
  名称：

  Novel thiol- and thioether-containing amino acids: cystathionine and homocysteine families

  摘要：

  Natural l-homocysteine and l,l-cystathionine, along with a series of unnatural analogues, have been prepared from l-aspartic and l-glutamic acid. Manipulation of the protected derivatives provided omega-iodoamino acids, which were used in thioalkylation reactions of sulfur nucleophiles, such as the ester of l-cysteine and potassium thioacetate.

  DOI：

  10.1007/s00726-012-1352-5
• 作为产物：
  描述：

  N-tert-Butoxycarbonyl-L-asaraginsaeure-α-allyl-β-phenacylester 在 sodium thiophenolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以51%的产率得到Boc-Asp-OAll
  参考文献：
  名称：

  Waldmann, Herbert; Kunz, Horst, Liebigs Annalen der Chemie, 1983, # 10, p. 1712 - 1725

  摘要：

  DOI：

文献信息

• Versatile Selective α-Carboxylic Acid Esterification of N-Protected Amino Acids and Peptides by Alcalase
  作者：Peter Quaedflieg、Timo Nuijens、Claudia Cusan、John Kruijtzer、Dirk Rijkers、Rob Liskamp

  DOI：10.1055/s-0028-1083362

  日期：——

  water, the industrial protease Alcalase allows selective synthesis of α-carboxylic acid methyl, ethyl, benzyl, allyl, 2-(trimethylsilyl)ethyl, and tert-butyl esters of amino acids and peptides under mild conditions in very high yields. The purified yields range from 72% to 92%. enzymes - amino acids - esterification - esters - protecting groups

  在连续去除水的条件下，工业蛋白酶Alcalase可以在温和条件下以很高的收率选择性合成氨基酸和肽的α-羧酸甲酯，乙酯，苄酯，烯丙基，2-（三甲基甲硅烷基）乙酯和叔丁酯。纯化的产率为72％至92％。 酶-氨基酸-酯化-酯-保护基
• Head-to-tail cyclization and use of Cα-allyl ester protection improves the yield of cyclic peptides synthesized by the oxime resin method
  作者：Afrodite Kapurniotu、John W. Taylor

  DOI：10.1016/s0040-4039(00)61589-7

  日期：1993.10

  Fully protected and C-terminal free cyclic (lactam-bridged) peptides are assembled by the oxime resin method in high yields and purity applying a four dimensional orthogonal (Boc/Bzl/Fmoc/Al) protection scheme and a head-to-tail cyclization strategy.

  通过肟树脂方法，采用二维正交（Boc / Bzl / Fmoc / Al）保护方案和从头到尾的环化反应，以高收率和高纯度组装完全保护的和C端自由环（内酰胺桥）肽战略。
• Synthesis of the 3′-terminal dinucleotide of tRNA aminoacylated with the unnatural ω-thioaspartic acid
  作者：Yuta Shinotsuka、Akihisa Ikehara、Tae Hirai、Kaname Sasaki

  DOI：10.1016/j.tetlet.2024.154988

  日期：2024.4

  is to incorporate the non-natural ω-thioaspartic acid (Asp) into proteins within a cell-free translation system and utilize the thiocarboxylic acids in side chains as handles for post-translational chemical modifications. As the initial step, in this study, we synthesized a protected dinucleotide (pdCpA) aminoacylated with Asp, corresponding to the 3′-end of tRNA. Furthermore, indications suggest that

  我们的目标是将非天然 ω-硫代天冬氨酸 (Asp) 整合到无细胞翻译系统中的蛋白质中，并利用侧链中的硫代羧酸作为翻译后化学修饰的手柄。作为第一步，在本研究中，我们合成了一个用 Asp 氨酰化的受保护二核苷酸 (pdCpA)，对应于 tRNA 的 3' 端。此外，有迹象表明氨酰化的 pdCpA 可以通过酸处理进行脱保护。
• Synthesis of the extracellular Ig domain I of Emmprin carrying a chitobiose unit
  作者：Hironobu Hojo、Jun Watabe、Yoshiaki Nakahara、Yuko Nakahara、Yukishige Ito、Kazuki Nabeshima、Bryan P Toole

  DOI：10.1016/s0040-4039(01)00342-2

  日期：2001.4

  The extracellular Ig domain I of Emmprin (34-94) carrying a chitobiose unit at Asn(44) was chemically synthesized. Boc-Asn with a benzyl-protected chitobiose unit was synthesized and used for the preparation of peptide thioester with the sequence of Emmprin (34-58) by Boc strategy. C-Terminal peptide amide (59-94) was also prepared by the solid-phase method. These segments were condensed by activation of the thioester group by silver ions to obtain a protected form of Emmprin (34-94)-NH2. After deprotection and air oxidation, the desired Emmprin (34-94)-NH2 with chitobiose was successfully obtained. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Bruch, Karsten von dem; Kunz, Horst, Angewandte Chemie, 1994, vol. 106, # 1, p. 87 - 89
  作者：Bruch, Karsten von dem、Kunz, Horst

  DOI：——

  日期：——