H-D-Val(Thz)-OEt | 143364-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: H-D-Val(Thz)-OEt
• 英文别名: Ethyl (R)-2-(1-amino-2-methylpropyl)thiazole-4-carboxylate；ethyl 2-[(1R)-1-amino-2-methylpropyl]-1,3-thiazole-4-carboxylate
• CAS: 143364-67-4
• 化学式: C₁₀H₁₆N₂O₂S
• 分子量: 228.315
• InChiKey: FMFFCNPPDJRMEX-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  H-D-Val(Thz)-OEt 在 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成
  参考文献：
  名称：

  Synthesis of the Bycroft−Gowland Structure of Micrococcin P1

  摘要：

  [GRAPHICS]We describe the chemical synthesis of the accepted structure of micrococcin P1, a member of the thiostrepton group of antibiotics, and we show that this architecture does not correspond to that of the natural product. Methods developed during the present study should greatly facilitate ongoing efforts centering on the determination of the actual structure of microccin P1, in addition to being applicable to the synthesis of more complex thiostrepton congeners.

  DOI：

  10.1021/ol991115e
• 作为产物：
  描述：

  Boc-D-缬氨酸 在 劳森试剂 、 吡啶 、 ammonium hydroxide 、 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 三氟乙酸酐 作用下， 生成 H-D-Val(Thz)-OEt
  参考文献：
  名称：

  含有α-脱氢氨基酸和脱氢肽结构的噻唑类化合物的简便合成

  摘要：

  首次实现了多种噻唑α-脱氢氨基酸、噻唑缬氨酸乙酯及其脱氢二肽和三肽的便捷合成，它们是微球菌P1和noshiheptide、大环肽类抗生素的重要组成部分和片段。

  DOI：

  10.1246/cl.1992.1005

文献信息

• Convenient Syntheses of Thiazoles Incorporated with α-Dehydroamino Acid and Dehydropeptide Structures
  作者：Yutaka Nakamura、Chung-gi Shin、Kazuyuki Umemura、Juji Yoshimura

  DOI：10.1246/cl.1992.1005

  日期：1992.6

  The convenient syntheses of various thiazole α-dehydroamino acids, thiazole valine ethyl ester, and their dehydrodiand tripeptides, which are important moieties and segment of micrococcin P1 and noshiheptide, macrocyclic peptide antibiotics, were first accomplished.

  首次实现了多种噻唑α-脱氢氨基酸、噻唑缬氨酸乙酯及其脱氢二肽和三肽的便捷合成，它们是微球菌P1和noshiheptide、大环肽类抗生素的重要组成部分和片段。
• Interaction of zinc(II) with the cyclic octapeptides, cyclo[Ile(Oxn)-D-Val(Thz)]2 and ascidiacyclamide, a cyclic peptide from Lissoclinum patella
  作者：Lisbeth Grøndahl、Nikolai Sokolenko、Giovanni Abbenante、David P. Fairlie、Graeme R. Hanson、Lawrence R. Gahan

  DOI：10.1039/a808836e

  日期：——

  The interactions between zinc salts and the naturally occurring cyclic octapeptide ascidiacyclamide in methanol, as well as a synthetic analogue cyclo[Ile(Oxn)-D-Val(Thz)]2, were monitored by 1H NMR and CD spectroscopy. Three zinc complexes were identified, their relative amounts depending on the nature of the anion (perchlorate, triflate or chloride) and the presence or absence of base. Binding constants for two of the zinc species were calculated from CD or 1H NMR spectra, [Zn(L – H)]+ (KZn(L–H) = [Zn(L – H)+]/[Zn2+][(L – H)–] = 107 ± 2 M–1; 95% methanol/5% water, 298.0 K, NEt3/HClO4 buffer 0.04 M) and [ZnLCl]+ (KZnClL = [ZnClL+]/[Zn2+][Cl–][L] = 107.2 ± 0.1 M–2; d3-methanol, 301 K).

  通过 1H NMR 和 CD 光谱监测了锌盐与甲醇中天然存在的环状八肽 ascidiacyclamide 以及合成类似物 cyclo[Ile(Oxn)-D-Val(Thz)]2 之间的相互作用。确定了三种锌络合物，其相对含量取决于阴离子的性质（高氯酸盐、三酸盐或氯化物）以及碱的存在与否。根据 CD 或 1H NMR 光谱计算出其中两种锌的结合常数：[Zn(L - H)]+ (KZn(L-H) = [Zn(L - H)+]/[Zn2+][(L - H)-] = 107 ± 2 M-1; 95% 甲醇/5% 水，298.0 K，NEt3/HClO4 缓冲液 0.04 M）和 [ZnLCl]+ （KZnClL = [ZnClL+]/[Zn2+][Cl-][L] = 107.2 ± 0.1 M-2；d3-甲醇，301 K）。
• Synthesis of the Bycroft−Gowland Structure of Micrococcin P1
  作者：Marco A. Ciufolini、Yong-Chun Shen

  DOI：10.1021/ol991115e

  日期：1999.12.1

  [GRAPHICS]We describe the chemical synthesis of the accepted structure of micrococcin P1, a member of the thiostrepton group of antibiotics, and we show that this architecture does not correspond to that of the natural product. Methods developed during the present study should greatly facilitate ongoing efforts centering on the determination of the actual structure of microccin P1, in addition to being applicable to the synthesis of more complex thiostrepton congeners.