Cbz-L-ala-L-ala-Cbz | 3886-07-5

• 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: Cbz-L-ala-L-ala-Cbz
• 英文别名: Z-Ala-Ala-OBn；Z-Ala-Ala-benzylester；Benzyloxycarbonyl-l-alanyl-l-alanine benzyl ester；benzyl (2S)-2-[[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate
• CAS: 3886-07-5
• 化学式: C₂₁H₂₄N₂O₅
• 分子量: 384.432
• InChiKey: UVFGJKZMNXFIME-HOTGVXAUSA-N

物化性质

• 熔点：
  141 °C
• 沸点：
  583.8±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  Cbz-L-ala-L-ala-Cbz 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 L-丙氨酰-L-丙氨酸
  参考文献：
  名称：

  Small peptides as modular catalysts for the direct asymmetric aldol reaction: ancient peptides with aldolase enzyme activity

  摘要：

  具有作为催化残基的主氨基的简单肽及其类似物，能以高立体选择性促进直接的不对称分子间醛醇反应，并生成最高达99% 对映体过量值的相应醛醇产物；这种高度模块化肽的内在能力可能解释了醛缩酶酶的初始分子进化过程。

  DOI：

  10.1039/b509920j
• 作为产物：
  描述：

  苄氧羰基-L-丙氨酸 在 N-甲基吗啉 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 Cbz-L-ala-L-ala-Cbz
  参考文献：
  名称：

  The small peptide-catalyzed direct asymmetric aldol reaction in water

  摘要：

  N 末端带有伯胺的简单模块化二肽和三肽可催化未修饰的酮和醛之间的水性不对称羟醛反应，为相应的 β-羟基酮提供在水中高达 86% ee 和在水介质中高达 99% ee 的 β-羟基酮。

  DOI：

  10.1039/b515880j

文献信息

• Small peptides as modular catalysts for the direct asymmetric aldol reaction: ancient peptides with aldolase enzyme activity
  作者：Weibiao Zou、Ismail Ibrahem、Pawel Dziedzic、Henrik Sundén、Armando Córdova

  DOI：10.1039/b509920j

  日期：——

  Simple peptides and their analogues having a primary amino group as the catalytic residue mediate the direct asymmetric intermolecular aldol reaction with high stereoselectivity and furnish the corresponding aldol products with up to 99% ee; this intrinsic ability of highly modular peptides may explain the initial molecular evolution of aldolase enzymes.

  具有作为催化残基的主氨基的简单肽及其类似物，能以高立体选择性促进直接的不对称分子间醛醇反应，并生成最高达99% 对映体过量值的相应醛醇产物；这种高度模块化肽的内在能力可能解释了醛缩酶酶的初始分子进化过程。
• Diphenyl (2,3-Dihydro-2-thioxo-3-benzoxazolyl)phosphonate: A New, Reactive Condensing Agent for the Synthesis of Amides, Esters, Peptides, and β-Lactams via Condensation
  作者：Mitsuru Ueda、Hideharu Mori

  DOI：10.1246/bcsj.65.1636

  日期：1992.6

  Diphenyl (2,3-dihydro-2-thioxo-3-benzoxazolyl)phosphonate (1) prepared from 2-benzoxazolethiol and diphenyl phosphorochloridate was proved to be a very useful condensing agent. A variety of amides, esters, and dipeptides were obtained in excellent yields. Furthermore, this reagent was successfully applied to the synthesis of β-lactams from β-amino acids.

  由 2-苯并恶唑硫醇和磷酸二苯酯制备的二苯基 (2,3-二氢-2-硫代-3-苯并恶唑基) 膦酸酯 (1) 被证明是一种非常有用的缩合剂。以极好的收率获得了多种酰胺、酯和二肽。此外，该试剂成功地应用于由β-氨基酸合成β-内酰胺。
• A Method for Cleaving an Allyl Protecting Group at the Amide Nitrogen of Peptides by One-Pot Olefin Isomerization−Oxidation
  作者：Kouki Kajihara、Mitsuhiro Arisawa、Satoshi Shuto

  DOI：10.1021/jo801915c

  日期：2008.12.5

  A facile method for N-deallylation at the amide nitrogen of peptides is described. One-pot deallylation of a substrate through ruthenium hydride-catalyzed terminal olefin isomerization and subsequent ozonolysis gave the corresponding deallylated product under mild conditions.

  描述了一种在肽的酰胺氮上进行N-去烯丙基化的简便方法。通过氢化物催化的末端烯烃异构化反应进行底物的一锅脱酯反应，然后进行臭氧分解，在温和的条件下得到相应的脱羧产物。
• Relative partial molar enthalpies and apparent molar volumes of dipeptides in aqueous solution
  作者：Shaun H. Dyke、Gavin R. Hedwig、Ian D. Watson

  DOI：10.1007/bf00647037

  日期：1981.5

  Enthalpies of dilution at 25°C of aqueous solutions of the dipeptides glycylglycine, glycylalanine and alanylalanine have been determined and used to calculate the partial molar enthalpies of the solvent water in the solutions. The partial molar volumes of these dipeptides are also reported. The results are discussed in terms of the likely solute-solvent interactions.

  已确定二肽甘氨酰甘氨酸、甘氨酰丙氨酸和丙氨酰丙氨酸的水溶液在 25°C 下的稀释焓，并用于计算溶液中溶剂水的偏摩尔焓。还报告了这些二肽的偏摩尔体积。结果根据可能的溶质-溶剂相互作用进行讨论。
• Conformational mimicry. 3. Synthesis and incorporation of 1,5-disubstituted tetrazole dipeptide analogs into peptides with preservation of chiral integrity: bradykinin
  作者：Janusz Zabrocki、James B. Dunbar、Keith W. Marshall、Mihaly V. Toth、Garland R. Marshall

  DOI：10.1021/jo00027a038

  日期：1992.1

  New synthetic procedures for preparing 1,5-disubstituted tetrazole dipeptide analogues, which are a conformational mimic of the cis amide bond, and incorporating these analogues into longer peptides, such as bradykinin, while maintaining chiral integrity are presented. The simple addition of the organic base, quinoline, to the reaction with PCl5 when generating an imidoyl chloride from the amide was effective in reducing racemization of the N-terminal amino acid residue of the protected tetrazole dipeptide to minimal levels. The resulting tetrazole dipeptide is quite sensitive to base, and the normal procedures of solid-phase synthesis for neutralization were sufficient to cause racemization of the alpha carbon on the C-terminal side of the tetrazole ring. The use of Z for amino protection and benzyl ester for carboxyl protection with differential removal of the Z group by HBr/HOAc has proven a practical route to a wide variety of tetrazole dipeptides. Immediate acylation of the tetrazole dipeptide with a Boc amino acid was necessary to prevent formation of the diketopiperazine, which is favored because of the cis conformation of the amide bond surrogate. Three bradykinin analogues, [L-Pro2-psi[CN4]-L-Ala3]-BK, [L-Ala6-psi[CN4]-L-Ala7]-BK, and [L-Ala6-psi[CN4]-D-Ala7]-BK, in which the peptide bond of a proline residue was replaced with the tetrazole surrogate, were prepared to illustrate the synthetic procedures. The availability of these procedures should increase the use of the tetrazole dipeptide analogue in molecular recognition studies.