H-D-Ala-Val-OMe | 95102-01-5

• 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-D-Ala-Val-OMe
• 英文别名: methyl (2S)-2-[[(2R)-2-aminopropanoyl]amino]-3-methylbutanoate
• CAS: 95102-01-5
• 化学式: C₉H₁₈N₂O₃
• 分子量: 202.254
• InChiKey: HFERNNXIGSVLPO-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  H-D-Ala-Val-OMe 在 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (S)-2-[(R)-2-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-propionylamino]-3-methyl-butyric acid
  参考文献：
  名称：

  Conformational variability in short acyclic peptides. Stabilization of multiple β-turn structures in organic solvents

  摘要：

  The conformational characteristics of three hexapeptides Boc-Leu-Xxx-Val-Leu-Aib-Val-OMe (Xxx = Ala 1, D-Ala 2, Gly 3; Aib = alpha-aminoisobutyryl) have been probed in CDCl3 solution by NMR methods using solvent perturbation of chemical shifts and radical broadening of NH resonances to delineate intramolecularly hydrogen bonded NH groups, Nuclear Overhauser effects (NOEs) provide additional information on preferred backbone conformations, The substituent at position 2 acts as a major conformational determinant, While a continuous 3(10) helical conformation is favoured for the peptide with Xxx = Ala, a multiple beta-turns conformation is supported by both NMR and CD data for the peptide with Xxx = D-Ala, In the peptide with Xxx = Gly CD and NMR data suggest that both 3(10) helical and multiple turns conformations are simultaneously populated, The results suggest that incorporation of D-amino acids and Aib residues into all L-sequences may prove useful in generating sequences containing multiple turns.

  DOI：

  10.1039/p29960002701
• 作为产物：
  描述：

  L-缬氨酸甲酯 在 sodium ethanolate 、 碳酸氢钠 、 巯基乙酸 作用下， 以 甲醇 、 氯仿 、 乙腈 为溶剂， 反应 2.75h， 生成 H-D-Ala-Val-OMe
  参考文献：
  名称：

  N -Nosyl-α-氨基酸在溶液相肽合成中的作用

  摘要：

  已经开发了在溶液相中高效且实用的肽合成方法。该过程是基于使用的p -nitrobenzenesulfonyl（硝基苯磺酰基）基团为α氨基酸的氨基官能团的保护。该方法的每一步，其特征在于通过收端基保护氨基功能，形成肽键并去除磺酰胺基，其特征在于高收率和最终产物的优异纯度。所描述的策略允许制备保持氨基酸前体的手性完整性的短肽序列。证明了nosyl基团与基于Fmoc的策略中使用的侧链保护基团的相容性。本文介绍的方法是一种替代策略，可为将来的肽合成提供优势。

  DOI：

  10.1016/j.tet.2007.05.121

文献信息

• Alanine Scan of the Peptide Antibiotic Feglymycin: Assessment of Amino Acid Side Chains Contributing to Antimicrobial Activity
  作者：Anne Hänchen、Saskia Rausch、Benjamin Landmann、Luigi Toti、Antje Nusser、Roderich D. Süssmuth

  DOI：10.1002/cbic.201300032

  日期：2013.3.18

  antibiotic feglymycin was performed by solution‐phase peptide synthesis to assess the significance of individual amino acid side chains for its biological activity. Antibacterial activity against Staphylococcus aureus and the inhibition of enzymes MurA and MurC depend on different amino acids.

  单模扫描：通过溶液相肽合成对肽抗生素海藻霉素进行丙氨酸扫描，以评估单个氨基酸侧链对其生物学活性的重要性。对金黄色葡萄球菌的抗菌活性和对酶MurA和MurC的抑制取决于不同的氨基酸。
• Conformational variability in short acyclic peptides. Stabilization of multiple β-turn structures in organic solvents
  作者：Satish Kumar Awasthi、Srinivasa Rao Raghothama、Padmanabhan Balaram

  DOI：10.1039/p29960002701

  日期：——

  The conformational characteristics of three hexapeptides Boc-Leu-Xxx-Val-Leu-Aib-Val-OMe (Xxx = Ala 1, D-Ala 2, Gly 3; Aib = alpha-aminoisobutyryl) have been probed in CDCl3 solution by NMR methods using solvent perturbation of chemical shifts and radical broadening of NH resonances to delineate intramolecularly hydrogen bonded NH groups, Nuclear Overhauser effects (NOEs) provide additional information on preferred backbone conformations, The substituent at position 2 acts as a major conformational determinant, While a continuous 3(10) helical conformation is favoured for the peptide with Xxx = Ala, a multiple beta-turns conformation is supported by both NMR and CD data for the peptide with Xxx = D-Ala, In the peptide with Xxx = Gly CD and NMR data suggest that both 3(10) helical and multiple turns conformations are simultaneously populated, The results suggest that incorporation of D-amino acids and Aib residues into all L-sequences may prove useful in generating sequences containing multiple turns.
• N-Nosyl-α-amino acids in solution phase peptide synthesis
  作者：Antonella Leggio、Maria Luisa Di Gioia、Francesca Perri、Angelo Liguori

  DOI：10.1016/j.tet.2007.05.121

  日期：2007.8

  excellent purity of the final products. The described strategy allows the preparation of short peptide sequences keeping the chiral integrity of amino acid precursors. Compatibility of nosyl group with the side-chain protecting groups used in Fmoc-based strategy is demonstrated. The method here presented is an alternative strategy that could provide advantages for future peptide synthesis.

  已经开发了在溶液相中高效且实用的肽合成方法。该过程是基于使用的p -nitrobenzenesulfonyl（硝基苯磺酰基）基团为α氨基酸的氨基官能团的保护。该方法的每一步，其特征在于通过收端基保护氨基功能，形成肽键并去除磺酰胺基，其特征在于高收率和最终产物的优异纯度。所描述的策略允许制备保持氨基酸前体的手性完整性的短肽序列。证明了nosyl基团与基于Fmoc的策略中使用的侧链保护基团的相容性。本文介绍的方法是一种替代策略，可为将来的肽合成提供优势。