叔丁氧羰基-丙氨酰-甘氨酸 | 28782-78-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 甘氨酸类衍生物
• 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
• 中文名称: 叔丁氧羰基-丙氨酰-甘氨酸
• 英文名称: N-(tert-butyloxycarbonyl)-(S)-alanylglycine
• 英文别名: Boc-Ala-Gly-OH；(S)-2-(2-((tert-Butoxycarbonyl)amino)propanamido)acetic acid；2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]acetic acid
• CAS: 28782-78-7
• 化学式: C₁₀H₁₈N₂O₅
• 分子量: 246.263
• InChiKey: PBGVVLQMNSPMKN-LURJTMIESA-N

物化性质

• 熔点：
  104-105 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  484.4±30.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2924199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8°C

制备方法与用途

(S)-2-[(2-((叔丁氧羰基)氨基)丙酰胺)乙酸]是甘氨酸（HY-Y0966）的衍生物[1]。

反应信息

• 作为反应物：
  描述：

  叔丁氧羰基-丙氨酰-甘氨酸 在 sodium hydroxide 、 氰基磷酸二乙酯 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Structural Analysis of .beta.-Turn Mimics Containing a Substituted 6-Aminocaproic Acid Linker

  摘要：

  A series of beta-turn models have been prepared consisting of the dipeptide Ala-Gly cyclized with all stereoisomers of 6-amino-3,5-dimethylcaproic acid and 6-amino-3-methylcaproic acid, as were related peptides based on Gly-Gly and Ala-Ala, The requisite linkers were made using routes featuring stereoselective ring-expansion reactions and the syntheses completed using standard methodology. A preliminary examination of these compounds has been carried out using NMR spectroscopy, circular dichroism, and, in several cases, X-ray crystallography. These studies indicate that, depending on linker stereochemistry, different proportions of type II and type I turns were observed in solution. Both type I and type II turns were observed in the solid state.

  DOI：

  10.1021/ja00124a001
• 作为产物：
  描述：

  Boc-Ala-Gly-OEt 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以58%的产率得到叔丁氧羰基-丙氨酰-甘氨酸
  参考文献：
  名称：

  Hartrodt; Neubert; Jakubke, Pharmazie, 1982, vol. 37, # 6, p. 403 - 407

  摘要：

  DOI：

文献信息

• 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Toluene-4-sulfonate (DMT/NMM/TsO⁻ ) Universal Coupling Reagent for Synthesis in Solution
  作者：Justyna Fraczyk、Zbigniew J. Kaminski、Joanna Katarzynska、Beata Kolesinska

  DOI：10.1002/hlca.201700187

  日期：2018.1

  environmentally‐friendly N‐triazinylammonium family of sulfonates, has been found to be a very effective coupling reagent for the synthesis of amides, esters and peptides in solution. This study confirms the usefulness of DMT/NMM/TsO− for peptide synthesis in solution, starting from Z‐, Fmoc‐, and Boc‐protected substrates as well as unnatural building blocks. Peptide synthesis with DMT/NMM/TsO− produced

  4-（4,6-二甲氧基-1,3,5-三嗪-2-基）-4-甲基吗啉的甲苯-4-磺酸酯（DMT / NMM / TSO - ），则廉价且环境友好的代表性构件Ñ磺酸的三叠氮基铵家族被发现是溶液中酰胺，酯和肽合成的非常有效的偶联剂。这项研究证实DMT / NMM / TSO的有用性-在溶液中的肽合成，从Z-，将Fmoc-，和起始Boc-保护的底物，以及不自然的构建块。用DMT / NMM / TsO进行肽合成-产量高，原油纯度高，外消旋化风险低。在所有情况下，都使用化学计量的试剂和标准的合成程序，而无需耗时的优化阶段或昂贵的色谱纯化。DMT / NMM / TSO -也被发现是用于使用片段偶联策略寡肽的合成中非常有用的。
• Design, synthesis and preliminary evaluation of α-sulfonyl γ-(glycinyl-amino)proline peptidomimetics as matrix metalloproteinase inhibitors
  作者：Jian Zhang、Xiaoyang Li、Yuqi Jiang、Jinhong Feng、Xiaoguang Li、Yingjie Zhang、Wenfang Xu

  DOI：10.1016/j.bmc.2013.12.025

  日期：2014.6

  A series of novel α-sulfonyl γ-(glycinyl-amino)proline peptidomimetic derivatives were designed, synthesized and assayed for their activities against matrix metalloproteinase-2 (MMP-2), aminopeptidase N (APN)/CD13 and HDACs. The results indicated that all the compounds exhibited highly selective inhibition against MMP-2 as compared with APN and HDACs. The antiproliferative activities of some compounds

  设计，合成和测定了一系列新型的α-磺酰基γ-（甘氨酰氨基）脯氨酸拟肽衍生物，它们对基质金属蛋白酶-2（MMP-2），氨基肽酶N（APN）/ CD13和HDAC的活性。结果表明，与APN和HDAC相比，所有化合物均显示出对MMP-2的高度选择性抑制。还研究了某些化合物对SKOV3，HL60和A549细胞的抗增殖活性。与对照LY52相比，在酶促抑制分析和基于细胞的分析中均具有优异活性的化合物12u可用作进一步开发MMP抑制剂的先导化合物。
• Click-Chemistry-Derived Tetracycline-Amino Acid Conjugates Exhibiting Exceptional Potency and Exclusive Recognition of the Reverse Tet Repressor
  作者：Igor Usai、Marcus Krueger、Jürgen Einsiedel、Wolfgang Hillen、Peter Gmeiner

  DOI：10.1002/cbic.200900710

  日期：2010.3.22

  TetRis: Applying click chemistry, a series of doxycycline–amino acid conjugates was synthesized. The C‐terminally linked phenylalanine derivative emerged as a highly selective effector for the reverse phenotype revTetR(B), and did not activate TetR. Interestingly, the test compound proved to be almost devoid of any antibacterial activity; which will be highly beneficial for future applications to control

  TetRis：应用点击化学，合成了一系列强力霉素-氨基酸共轭物。C端连接的苯丙氨酸衍生物作为反向表型revTetR（B）的高度选择性效应子出现，并且没有激活TetR。有趣的是，被测化合物几乎没有任何抗菌活性。这对于控制细菌系统中基因表达的未来应用将是非常有益的。
• Copper(I)-Mediated Denitrogenative Macrocyclization for the Synthesis of Cyclic α₃ β-Tetrapeptide Analogues
  作者：Chun-Chi Chen、Sheng-Fu Wang、Yung-Yu Su、Yuya A. Lin、Po-Chiao Lin

  DOI：10.1002/asia.201700339

  日期：2017.6.19

  α3β‐tetrapeptide analogues that contain important biological properties and results in rich structural information being obtained for conformational studies. With the success of this copper(I)‐catalyzed macrocyclization, two histone deacetylase inhibitor analogues consisting of the cyclic α3β‐tetrapeptide framework have been successfully synthesized.

  铜（I）介导的脱氮反应已成功开发，用于制备环状四肽。关键的反应性中间体酮亚胺通过末端胺基的攻击触发分子内环化反应，生成具有generate键的内部β-氨基酸。本文所开发的化学提供用于循环α的制备一种新的合成路线3包含重要的生物学特性和丰富的结构信息结果的构象研究而获得β-四肽类似物。与此铜（I） -催化大环化的成功，2代由环状α的组蛋白脱乙酰酶抑制剂的类似物3 β-四肽框架已被成功地合成。
• Cyclic prodrugs of peptides and peptide nucleic acids having improved
  申请人：The University of Kansas

  公开号：US05672584A1

  公开（公告）日：1997-09-30

  Provided are cyclic prodrugs of biologically active peptides and peptide nucleic acids exhibiting improved cell membrane permeability and enzymatic stability, containing 3-(2'-hydroxy-4',6'-dimethyl phenyl)-3,3-dimethyl propionic acid and its deriveatives and acyloxyalkoxy linkers. Also provided are pharmaceutical compositions containing effective amounts of these cyclic prodrugs in combination with pharmaceutically acceptable carriers, excipients, or diluents.

  提供了生物活性肽和肽核酸的环状前药，表现出改善的细胞膜渗透性和酶稳定性，含有3-(2'-羟基-4',6'-二甲基苯基)-3,3-二甲基丙酸及其衍生物和酰氧烷氧基连接剂。还提供了含有这些环状前药有效量的药物组合物，与药用可接受的载体、赋形剂或稀释剂结合。