Fmoc-Cys((O2)Me)-OH | 244132-29-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Cys((O2)Me)-OH
• 英文别名: N-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-3-(methanesulfonyl)-L-alanine；(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylsulfonylpropanoic acid
• CAS: 244132-29-4
• 化学式: C₁₉H₁₉NO₆S
• 分子量: 389.429
• InChiKey: SGRFSKFFNRFQMF-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-芴甲氧羰基-S-甲基-L-半胱氨酸 在 Oxone 作用下， 以 甲醇 、 水 为溶剂， 反应 1.5h， 以96%的产率得到Fmoc-Cys((O2)Me)-OH
  参考文献：
  名称：

  Sc（OTf）3介导的硫醚的轻度和高度化学选择性氧化。

  摘要：

  [反应：见正文]催化Sc（OTf）（3）大大提高了过氧化氢介导的烷基芳基硫醚和甲基半胱氨酸肽的单氧化效率。该方法收率高，可与许多广泛使用的保护基团兼容，适用于固相应用，且过氧化反应最少。

  DOI：

  10.1021/ol026947i

文献信息

• Thrombospondin 1-binding peptide
  申请人：DAIICHI SANKYO COMPANY, LIMITED

  公开号：US11149066B2

  公开（公告）日：2021-10-19

  Provided is a compound that can promote angiogenesis by inhibiting the function of TSP1, and is useful for the treatment or prophylaxis of diseases such as critical limb ischemia. Specifically provided is a macrocyclic polypeptide represented by formula (I) [wherein A is selected from the linking groups A1 to A6; Xaa1 is a residue of an aliphatic amino acid, an aromatic amino acid, a basic amino acid, a neutral amino acid, or an acidic amino acid, or is absent; Xaa2 is a residue of an aromatic amino acid or a neutral amino acid; Xaa3 is a residue of an aliphatic amino acid, an aromatic amino acid, or a basic amino acid; Xaa4 is Ser, Thr, Ala, or mS; Xaa5 is Gly or Ser; Xaa6 is a residue of a basic amino acid or a neutral amino acid; Xaa7 is a residue of a neutral amino acid or an acidic amino acid; Xaa8 is a residue of an aromatic amino acid; Xaa9 is a residue of an aliphatic amino acid, a neutral amino acid, or an aromatic amino acid; Xaa10 is a residue of a basic amino acid, an aliphatic amino acid, an aromatic amino acid, or a neutral amino acid; Xaa11 is a residue of an aromatic amino acid; and Xaa12 is a residue of an aliphatic amino acid, an aromatic amino acid, or a basic amino acid], or a pharmacologically acceptable salt thereof.

  本发明提供了一种化合物，该化合物可通过抑制 TSP1 的功能促进血管生成，并可用于治疗或预防危重肢体缺血等疾病。 具体而言，提供了一种由式（I）代表的大环多肽 [其中 A 选自连接基团 A1 至 A6；Xaa1 是脂肪族氨基酸、芳香族氨基酸、碱性氨基酸、中性氨基酸或酸性氨基酸的残基，或者不存在；Xaa2 是芳香族氨基酸或中性氨基酸的残基；Xaa3 是脂肪族氨基酸、芳香族氨基酸或碱性氨基酸的残基； Xaa4 是 Ser、Thr、Ala 或 mS； Xaa5 是 Gly 或 Ser； Xaa6 是碱性氨基酸或中性氨基酸的残基；Xaa7 是中性氨基酸或酸性氨基酸的残基； Xaa8 是芳香族氨基酸的残基； Xaa9 是脂肪族氨基酸、中性氨基酸或芳香族氨基酸的残基；Xaa10 是碱性氨基酸、脂肪族氨基酸、芳香族氨基酸或中性氨基酸的残基； Xaa11 是芳香族氨基酸的残基；以及 Xaa12 是脂肪族氨基酸、芳香族氨基酸或碱性氨基酸的残基]，或其药理学上可接受的盐。
• THROMBOSPONDIN 1-BINDING PEPTIDE
  申请人：DAIICHI SANKYO COMPANY, LIMITED

  公开号：US20200131230A1

  公开（公告）日：2020-04-30

  Provided is a compound that can promote angiogenesis by inhibiting the function of TSP1, and is useful for the treatment or prophylaxis of diseases such as critical limb ischemia. Specifically provided is a macrocyclic polypeptide represented by formula (I) [wherein A is selected from the linking groups A 1 to A 6 ; X aa1 is a residue of an aliphatic amino acid, an aromatic amino acid, a basic amino acid, a neutral amino acid, or an acidic amino acid, or is absent; X aa2 is a residue of an aromatic amino acid or a neutral amino acid; X aa3 is a residue of an aliphatic amino acid, an aromatic amino acid, or a basic amino acid; X aa4 is Ser, Thr, Ala, or m S; X aa5 is Gly or Ser; X aa6 is a residue of a basic amino acid or a neutral amino acid; X aa7 is a residue of a neutral amino acid or an acidic amino acid; X aa8 is a residue of an aromatic amino acid; X aa9 is a residue of an aliphatic amino acid, a neutral amino acid, or an aromatic amino acid; X aa10 is a residue of a basic amino acid, an aliphatic amino acid, an aromatic amino acid, or a neutral amino acid; X aa11 is a residue of an aromatic amino acid; and X aa12 is a residue of an aliphatic amino acid, an aromatic amino acid, or a basic amino acid], or a pharmacologically acceptable salt thereof.
• US6372883B1
  申请人：——

  公开号：US6372883B1

  公开（公告）日：2002-04-16
• Mild and Highly Chemoselective Oxidation of Thioethers Mediated by Sc(OTf)₃
  作者：Mizio Matteucci、Gurdip Bhalay、Mark Bradley

  DOI：10.1021/ol026947i

  日期：2003.2.1

  [reaction: see text] Catalytic Sc(OTf)(3) greatly increases the efficiency of hydrogen peroxide mediated monooxidation of alkyl-aryl sulfides and methyl cysteine containing peptides. The method is high yielding, compatible with many widely used protecting groups, suitable for solid-phase applications and proceeds with minimum over-oxidation.

  [反应：见正文]催化Sc（OTf）（3）大大提高了过氧化氢介导的烷基芳基硫醚和甲基半胱氨酸肽的单氧化效率。该方法收率高，可与许多广泛使用的保护基团兼容，适用于固相应用，且过氧化反应最少。