Boc-Ala-Gly-Gly-OBzl | 73870-83-4

• 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-Ala-Gly-Gly-OBzl
• 英文别名: benzyl 2-[[2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]acetyl]amino]acetate
• CAS: 73870-83-4
• 化学式: C₁₉H₂₇N₃O₆
• 分子量: 393.44
• InChiKey: UMANWHSLWVBVFN-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Ala-Gly-Gly-OBzl 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 [2-((S)-2-Amino-propionylamino)-acetylamino]-acetic acid benzyl ester; hydrochloride
  参考文献：
  名称：

  Synthesis of a Partial Sequence of Proinsulin Using the A-Chain of Natural Insulin. III. Synthesis of a Peptide Corresponding to Positions 41–81 of Bovine Proinsulin

  摘要：

  为了合成牛前胰岛素，使用了与天然牛胰岛素A链的S-磺酸盐合成的Leu–Glu–Gly–Pro–Pro–Gln–Lys[Z(2-Cl)]–Arg–A链的S-磺酸盐，其对应于牛前胰岛素的位置53–81，并将其与Boc–Ala–Leu–Glu(OBut)–Leu–Ala–Gly–Gly–Pro–Gly–Ala–Gly–Gly–N3偶联。在去除所得物质的保护基团后，对应于牛前胰岛素位置41–81的Ala–Leu–Glu–Leu–Ala–Gly–Gly–Pro–Gly–Ala–Gly–Gly–Leu–Glu–Gly–Pro–Pro–Gln–Lys[Z(2-Cl)]–Arg–A链的S-磺酸盐，通过在QAE-Sephadex A-25上的色谱法进行纯化。

  DOI：

  10.1246/bcsj.53.197
• 作为产物：
  描述：

  Boc-Ala-Gly-OBzl 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 Boc-Ala-Gly-Gly-OBzl
  参考文献：
  名称：

  Synthesis of a Novel Esterase-Sensitive Cyclic Prodrug of a Hexapeptide Using an (Acyloxy)alkoxy Promoiety

  摘要：

  Synthetic methodology for preparing novel esterase-sensitive cyclic prodrugs of peptides with increased protease stability and cell membrane permeability compared to linear peptides is described. Cyclic prodrug 1 of the hexapeptide H-Trp-Ala-Gly-Gly-Asp-Ala-OH linked by the N-terminal amino group to the C-terminal carboxyl group via an (acyloxy)alkoxy promoiety was synthesized. A convergent synthetic approach involving Boc[[(alaninyloxy)methyl]carbonyl]-N-tryptophan (2) and H-Ala-Gly-Gly-Asp(OBzl)-OTce (3) was used. The key fragment 2 has the promoiety inserted between the Ala and the Trp residues. Fragment 3 was synthesized by a solution-phase approach using standard Boc-amino acid chemistry. These fragments were coupled to produce the protected linear hexapeptide, which after deprotection was cyclized using standard high-dilution techniques to yield cyclic prodrug 1. In pH 7.4 buffer (HBSS) at 37 degrees C, cyclic prodrug 1 was shown to degrade quantitatively to the hexapeptide (t(1/2) = 206 +/- 11 min). The rate of hydrolysis of cyclic prodrug 1 was significantly faster in human blood (t(1/2) = 132 +/- 4 min) than in HBSS. Paraoxon, a known inhibitor of esterases, slowed this hydrolysis of cyclic prodrug 1 to a value (t(1/2) = 198 +/- 9 min) comparable to the chemical stability. In human blood, cyclic prodrug 1 was shown to be 25-fold more stable than the linear hexapeptide.

  DOI：

  10.1021/jo961696a

文献信息

• Development of Supramolecular Organo-Gel Based on Tripeptide Skeletons
  作者：Eriko Azuma、Kouji Kuramochi、Kazunori Tsubaki

  DOI：10.1248/cpb.58.680

  日期：——

  Boc-Ser-Val-Gly-OCH2Ph (31) showed high gelation abilities in the aromatic solvents, particularly in toluene. The minimum gelation concentration of 31 in toluene was 10 mg/ml, suggesting that 2500 molecules of toluene were immobilized by each molecule of the tripeptide 31. The FT-IR data indicated that formation of antiparallel β-sheets through intermolecular hydrogen bonding was central to the generation of nanofibers during gelation.

  Boc-Ser-Val-Gly-OCH2Ph (31) 在芳香族溶剂中显示出强大的成胶能力，尤其是在甲苯中。31在甲苯中的最低成胶浓度为10 mg/ml，这意味着每分子三肽31固定了2500个甲苯分子。傅里叶变换红外光谱数据显示，通过分子间氢键形成反平行β-折叠是成胶过程中产生纳米纤维的关键。
• 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.

  提供了具有改善细胞膜渗透性和酶稳定性的生物活性肽和肽核酸的环状前药，包含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基烷氧基连接剂。还提供了含有这些环状前药的有效量的制药组合物，其中包含药用可接受载体，辅料或稀释剂。
• A Novel Resin Linker for Solid-Phase Peptide Synthesis Which Can Be Cleaved Using Two Sequential Mild Reactions
  作者：Ailian Zheng、Daxian Shan、Xuling Shi、Binghe Wang

  DOI：10.1021/jo990770x

  日期：1999.10.1

  The interest in developing new linkers for solid-phase peptide and organic synthesis has increased tremendously as a result of the rapid development of combinatorial chemistry. Herein, we report the development of a new redox-sensitive linker for solid-phase peptide synthesis. This linker can be readily cleaved under mild conditions by using two sequential mild reactions, a reduction followed by a base (Bu4N+F-)-catalyzed cyclic ether formation. By using this new linker, two short peptides, a tetrapeptide [Boc-Trp-Ala-Gly-Gly-OH] and a pentapeptide [Boc-Asn-Ala-Ser(OBn)-Gly-Glu(OBn)-OH)], were synthesized. Because the cleavage does not use acidic conditions, this resin linker provides an alternative when acidic conditions are not desirable. Furthermore, the cleavage conditions do not affect most of the side chain protecting group. Therefore, the peptides synthesized can be used for the segment synthesis of larger peptides without the need to reprotect the side chain functional groups.