(S)-methyl 2-((S)-3-(benzyloxy)-2-(benzyloxycarbonylamino)propanamido)-3-hydroxypropanoate | 75893-22-0

• 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: (S)-methyl 2-((S)-3-(benzyloxy)-2-(benzyloxycarbonylamino)propanamido)-3-hydroxypropanoate
• 英文别名: Z-Ser(Bzl)-Ser-OMe；Z-Ser(OBz)-Ser-OMe；methyl (2S)-3-hydroxy-2-[[(2S)-3-phenylmethoxy-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate
• CAS: 75893-22-0
• 化学式: C₂₂H₂₆N₂O₇
• 分子量: 430.458
• InChiKey: FMAISHLEAIGCDI-OALUTQOASA-N

物化性质

• 熔点：
  108-110 °C
• 沸点：
  682.1±55.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  123.19
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-((S)-3-(benzyloxy)-2-(benzyloxycarbonylamino)propanamido)-3-hydroxypropanoate 在 盐酸 、 亚硝酸特丁酯 、 NHNH₂*H₂O 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 40.17h， 生成 Z-Ser(Bzl)-Ser-Ser-Lys(Boc)-OMe
  参考文献：
  名称：

  Human chorionic gonadotropin. III. Synthesis of a dotriacontapeptide corresponding to the C-terminal sequence 116-147 of the .BETA.-subunit of human chorionic gonadotropin (hCG).

  摘要：

  通过分步片段缩合，将五个片段[Z-Gln-Asp(OBzl)-OH、Z-Ser(Bzl)-Ser-Ser-Lys(Boc)-NHNH2、Z-Ala-Pro-Pro-NHNHBoc、Z-Ser(Bzl)-Leu-Pro-NHNHBoc 和 Z-Ser(Bzl)-Pro-Ser-NHNH2]连接到前一篇论文中报告的十六肽上，合成了该化合物。

  DOI：

  10.1248/cpb.28.2699
• 作为产物：
  描述：

  N-苄氧羰基-L-丝氨酸 在 氯甲酸乙酯 、 sodium hydride 、 三乙胺 作用下， 反应 7.42h， 生成 (S)-methyl 2-((S)-3-(benzyloxy)-2-(benzyloxycarbonylamino)propanamido)-3-hydroxypropanoate
  参考文献：
  名称：

  Human chorionic gonadotropin. III. Synthesis of a dotriacontapeptide corresponding to the C-terminal sequence 116-147 of the .BETA.-subunit of human chorionic gonadotropin (hCG).

  摘要：

  通过分步片段缩合，将五个片段[Z-Gln-Asp(OBzl)-OH、Z-Ser(Bzl)-Ser-Ser-Lys(Boc)-NHNH2、Z-Ala-Pro-Pro-NHNHBoc、Z-Ser(Bzl)-Leu-Pro-NHNHBoc 和 Z-Ser(Bzl)-Pro-Ser-NHNH2]连接到前一篇论文中报告的十六肽上，合成了该化合物。

  DOI：

  10.1248/cpb.28.2699

文献信息

• Conversion of serine and threonine residues into α-acyloxy-, a-alkylthio-, and α- halogenoglycine moieties: A new strategy for the modification of peptides
  作者：Gregor Apitz、Wolfgang Steglich

  DOI：10.1016/s0040-4039(00)79711-5

  日期：1991.7

  Selective modification of serine and threonine containing peptides is accomplished by oxidation with lead tetraacetate. Conversion of the derived a-acyloxyglycine derivatives into α-alkylthio and α-halogenoglycine residues offers a novel synthetic route to modified glycyl peptides, enzyme inhibitors, and dehydropeptides.

  含丝氨酸和苏氨酸的肽的选择性修饰是通过用四乙酸铅氧化来实现的。将衍生的α-酰氧基甘氨酸衍生物转化为α-烷硫基和α-卤代甘氨酸残基提供了一种新的合成途径，用于修饰的糖基肽，酶抑制剂和脱氢肽。
• Hydrogen-Bond-Induced Hysteresis in the Compression/Relaxation of Monolayer Films
  作者：Jennifer L. Sorrells、Fredric M. Menger

  DOI：10.1021/ja803491y

  日期：2008.8.1

  Two stereoisomers of surfactants were synthesized in which a diketopiperazine ring was inserted between a hydrocarbon chain (variable length) and an anionic headgroup. It was found (by HPLC, conductivity, surface tension, and diffusion NMR) that these compounds have low solubilities in water, remarkably high Krafft temperatures, and low critical micelle concentrations. Of particular interest were the pressure/area isotherms of insoluable monolayers of nonionic analogues of the amphiphiles. These isotherms showed an unprecedented hysteresis but only during the first compression/relaxation cycle. Additional cycles were normal in that they lacked the original hysteresis. These results were attributed to diketopiperazine rings that initially lie flat on the water surface at the air/water interface. Compression flips the diketopiperazine rings so that they now reside roughly perpendicular to the interface in the stable hydrogen-bonded orientation where the rings occupy far less space.