H-Thr-Ala-OMe | 45120-25-0

• 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: H-Thr-Ala-OMe
• 英文别名: methyl (2S)-2-[[(2S,3R)-2-amino-3-hydroxybutanoyl]amino]propanoate
• CAS: 45120-25-0
• 化学式: C₈H₁₆N₂O₄
• 分子量: 204.226
• InChiKey: OPFKQEOEFMVGBK-JKUQZMGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  H-Thr-Ala-OMe 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 苯甲醚 、 三乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 Boc-Ala-Cys(Ad)-Asp-Thr-Ala-OMe
  参考文献：
  名称：

  肽的研究。CXXXV。制备用于合成人降钙素基因相关肽（hCGRP）的七个肽片段。

  摘要：

  七个肽片段通过已知的酰胺形成反应合成，作为溶液相合成与人类降钙素基因相关肽（hCGRP）完整氨基酸序列相对应的七十氨基肽酰胺的构建块。采用了S-1-亚当烷基半胱氨酸 [O. Nishimura, C. Kitada, 和 M. Fujino, Chem. Pharm. Bull., 26, 1576 (1978)]，同时使用了具有保护基团的氨基酸衍生物，这些保护基团可通过1 M三氟甲磺酸-硫醇醚在三氟乙酸中去除。

  DOI：

  10.1248/cpb.34.603
• 作为产物：
  描述：

  Z-Thr-Ala-OMe 在 氢气 作用下， 生成 H-Thr-Ala-OMe
  参考文献：
  名称：

  Amino acids and peptides. XIV Synthesis and biological activity of three S-peptide analogues of bovine pancreatic ribonuclease A (RNase A).

  摘要：

  采用片段缩合法合成了牛胰腺核糖核酸酶 A（RNase A）的三种 S 肽类似物，即 [Nle1] [Lys7] S 肽（I）、[Lys1] [Nle7] S 肽（II）和 [Nle1] [Nle7] S 肽（III），并考察了它们重新激活 S 蛋白的能力。结果发现，Lys1 和 Lys7 都在 S 蛋白的再活化过程中发挥作用。

  DOI：

  10.1248/cpb.35.468

文献信息

• Amino acids and peptides. XIV Synthesis and biological activity of three S-peptide analogues of bovine pancreatic ribonuclease A (RNase A).
  作者：NAOKI TENO、SATOSHI TSUBOI、TOMOKO SHIMAMURA、YOSHIO OKADA、YOSHIMI YANAGIDA、MAKIKO YOSHINAGA、KAZUKO OHGI、MASACHIKA IRIE

  DOI：10.1248/cpb.35.468

  日期：——

  Three S-peptide analogues of bovine pancreatic ribonuclease A (RNase A), [Nle1] [Lys7] S-peptide (I), [Lys1] [Nle7] S-peptide (II) and [Nle1] [Nle7] S-peptide (III), were synthesized by the fragment condensation method and their ability to reactivate S-protein was examined. It was found that Lys1 and Lys7 both have roles in the reactivation of S-protein.

  采用片段缩合法合成了牛胰腺核糖核酸酶 A（RNase A）的三种 S 肽类似物，即 [Nle1] [Lys7] S 肽（I）、[Lys1] [Nle7] S 肽（II）和 [Nle1] [Nle7] S 肽（III），并考察了它们重新激活 S 蛋白的能力。结果发现，Lys1 和 Lys7 都在 S 蛋白的再活化过程中发挥作用。
• Studies on peptides. CXXXV. Preparation of seven peptide fragments for the synthesis of human calcitonin gene-related peptide (hCGRP).
  作者：NOBUTAKA FUJII、AKIRA OTAKA、SUSUMU FUNAKOSHI、MOTOYOSHI NOMIZU、KENICHI AKAJI、HARUAKI YAJIMA、KOUKI KITAGAWA、TADASHI AKITA、KENSHI ANDO、TATSUHIKO KAWAMOTO

  DOI：10.1248/cpb.34.603

  日期：——

  Seven peptide fragments were synthesized by known amide-forming reactions as building blocks for the solution-phase synthesis of the heptatriacontapeptide amide corresponding to the entire amino acid sequence of human calcitonin gene-related peptide (hCGRP). S-1-Adamantyl-cysteine [O. Nishimura, C. Kitada, and M. Fujino, Chem. Pharm. Bull., 26, 1576 (1978)] was employed, together with amino acid derivatives bearing protecting groups removable by 1 M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid.

  七个肽片段通过已知的酰胺形成反应合成，作为溶液相合成与人类降钙素基因相关肽（hCGRP）完整氨基酸序列相对应的七十氨基肽酰胺的构建块。采用了S-1-亚当烷基半胱氨酸 [O. Nishimura, C. Kitada, 和 M. Fujino, Chem. Pharm. Bull., 26, 1576 (1978)]，同时使用了具有保护基团的氨基酸衍生物，这些保护基团可通过1 M三氟甲磺酸-硫醇醚在三氟乙酸中去除。
• Impact of Dehydroamino Acids on the Structure and Stability of Incipient 3₁₀-Helical Peptides
  作者：Daniel Joaquin、Michael A. Lee、David W. Kastner、Jatinder Singh、Shardon T. Morrill、Gracie Damstedt、Steven L. Castle

  DOI：10.1021/acs.joc.9b02747

  日期：2020.2.7

  A comparative study of the impact of small, medium-sized, and bulky alpha,beta-dehydroamino acids (Delta AAs) on the structure and stability of Balarams incipient 3(10)-helical peptide (1) is reported. Replacement of the N-terminal Aib residue of 1 with a Delta AA afforded peptides 2a-c that maintained the 3(10)-helical shape of 1. In contrast, installation of a Delta AA in place of Aib-3 yielded peptides 3a-c that preferred a beta-sheet-like conformation. The impact of the Delta AA on peptide structure was independent of size, with small (Delta Ala), medium-sized (Z-Delta Abu), and bulky (Delta Val) Delta AAs exerting similar effects. The proteolytic stabilities of 1 and its analogs were determined by incubation with Pronase. Z-Delta Abu and Delta Val increased the resistance of peptides to proteolysis when incorporated at the 3-position and had negligible impact on stability when placed at the 1-position, whereas Delta Ala-containing peptides degraded rapidly regardless of position. Exposure of peptides 2a-c and 3a-c to the reactive thiol cysteamine revealed that Delta Ala-containing peptides underwent conjugate addition at room temperature, while Z-Delta Abu- and Delta Val-containing peptides were inert even at elevated temperatures. These results suggest that both bulky and more accessible medium-sized Delta AAs should be valuable tools for bestowing rigidity and proteolytic stability on bioactive peptides.