(-)-(2S)-2-amino-6-hydroxy-4-oxahexanoic acid | 126595-73-1

• 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: (-)-(2S)-2-amino-6-hydroxy-4-oxahexanoic acid
• 英文别名: L-Serine, O-(2-hydroxyethyl)-；(2S)-2-amino-3-(2-hydroxyethoxy)propanoic acid
• CAS: 126595-73-1
• 化学式: C₅H₁₁NO₄
• 分子量: 149.147
• InChiKey: OKNHGXUPNOETTM-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(2S)-2-amino-6-hydroxy-4-oxahexanoic acid 在 甲酸 、 4-甲基苯磺酸吡啶 、 sodium carbonate 作用下， 生成 N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)-L-serine
  参考文献：
  名称：

  AMINO ACID HAVING FUNCTIONAL GROUP CAPABLE OF INTERMOLECULAR HYDROGEN BONDING, PEPTIDE COMPOUND CONTAINING SAME AND METHOD FOR PRODUCTION THEREOF

  摘要：

  It has been found that the membrane permeability of peptide compounds can be improved by making at least one of amino acids constituting the peptide compound be an amino acid having a side chain capable of forming an intramolecular hydrogen bond.

  公开号：

  US20230096766A1
• 作为产物：
  描述：

  (+)-(2S)-6-benzyloxy-2-(N-benzyloxycarbonylamino)-4-oxahexanoic acid 生成 (-)-(2S)-2-amino-6-hydroxy-4-oxahexanoic acid
  参考文献：
  名称：

  AMINO ACID HAVING FUNCTIONAL GROUP CAPABLE OF INTERMOLECULAR HYDROGEN BONDING, PEPTIDE COMPOUND CONTAINING SAME AND METHOD FOR PRODUCTION THEREOF

  摘要：

  It has been found that the membrane permeability of peptide compounds can be improved by making at least one of amino acids constituting the peptide compound be an amino acid having a side chain capable of forming an intramolecular hydrogen bond.

  公开号：

  US20230096766A1

文献信息

• Synthesis of disulfide surrogate peptides incorporating an ethylene glycol bridge
  作者：Xiao-Xiong Wei、Ji-Bin Cui、Rui Zhao、Jie Luo、Yi-Ming Li、Donald Bierer、Jing Shi

  DOI：10.1039/d2nj05290c

  日期：——

  disulfide-rich peptides. In this study, we report a new diaminodiacid containing ethylene glycol bridge (EG-DADA), obtained primarily through the ring-opening addition reaction of aziridine derivatives with hydroxyl groups. The practicability and oxidation stability of this novel diaminodiacid have been illustrated by the synthesis of disulfide bond mimics of tachyplesin I and α-ImI. The development of EG-DADA

  通过二氨基二酸策略用代谢稳定的等排物取代二硫键已被证明是提高富含二硫键的肽的稳定性的有效且灵活的方法。在这项研究中，我们报道了一种新的含有乙二醇桥的二氨基二酸 (EG-DADA)，主要通过氮丙啶衍生物与羟基的开环加成反应获得。通过合成 tachyplesin I和α-ImI的二硫键模拟物，说明了这种新型二氨基二酸的实用性和氧化稳定性。EG-DADA的开发丰富了醚基二氨基二酸，为二硫化物替代肽的构建提供了灵活的选择。
• Larsson, Ulf; Carlson, Rolf, Acta Chemica Scandinavica, 1994, vol. 48, # 6, p. 511 - 516
  作者：Larsson, Ulf、Carlson, Rolf

  DOI：——

  日期：——
• AMINO ACID HAVING FUNCTIONAL GROUP CAPABLE OF INTERMOLECULAR HYDROGEN BONDING, PEPTIDE COMPOUND CONTAINING SAME AND METHOD FOR PRODUCTION THEREOF
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US20230096766A1

  公开（公告）日：2023-03-30

  It has been found that the membrane permeability of peptide compounds can be improved by making at least one of amino acids constituting the peptide compound be an amino acid having a side chain capable of forming an intramolecular hydrogen bond.