(2R,3R)-2-(dimethylamino)-3-methylpentanoic acid | 174785-99-0

• 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: (2R,3R)-2-(dimethylamino)-3-methylpentanoic acid
• CAS: 174785-99-0
• 化学式: C₈H₁₇NO₂
• 分子量: 159.228
• InChiKey: OQJJVXKMPUJFJK-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-D-allo-isoleucine 、 (2R,3R)-2-(dimethylamino)-3-methylpentanoic acid 、 dimethyl-L-alloisoleucine 、 (2S,3S)-2-(二甲氨基)-3-甲基戊酸 、 2-溴代-2-乙酰基萘 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 生成 (2-naphthalen-2-yl-2-oxoethyl) (2R,3R)-2-(dimethylamino)-3-methylpentanoate 、 (2-naphthalen-2-yl-2-oxoethyl) (2R,3S)-2-(dimethylamino)-3-methylpentanoate 、 (2-naphthalen-2-yl-2-oxoethyl) (2S,3R)-2-(dimethylamino)-3-methylpentanoate 、 N,N-dimethyl-L-isoleucine 2-naphthacyl ester
  参考文献：
  名称：

  Symplocin A, a Linear Peptide from the Bahamian CyanobacteriumSymplocasp. Configurational Analysis ofN,N-Dimethylamino Acids by Chiral-Phase HPLC of Naphthacyl Esters

  摘要：

  The absolute stereostructures of the components of symplocin A (3), a new N,N-dimethyl-terminated peptide from the Bahamian cyanobacterium Symploca sp., were assigned from spectroscopic analysis, including MS, 2D NMR, and Marfey's analysis. The complete absolute configuration of symplocin A, including the unexpected D-configurations of the terminal N,N-dimethylisoleucine and valic acid residues, was assigned by chiral-phase HPLC of the corresponding 2-naphthacyl esters, a highly sensitive, complementary strategy for assignment of N-blocked peptide residues where Marfey's method is ineffectual or other methods fall short. Symplocin A exhibited potent activity as an inhibitor of cathepsin E (IC50 300 pM).

  DOI：

  10.1021/np200861n
• 作为产物：
  描述：

  聚合甲醛 、 D-异亮氨酸 在 palladium 10% on activated carbon 、 氢气 作用下， 以 水 为溶剂， 生成 (2R,3R)-2-(dimethylamino)-3-methylpentanoic acid
  参考文献：
  名称：

  Symplocin A, a Linear Peptide from the Bahamian CyanobacteriumSymplocasp. Configurational Analysis ofN,N-Dimethylamino Acids by Chiral-Phase HPLC of Naphthacyl Esters

  摘要：

  The absolute stereostructures of the components of symplocin A (3), a new N,N-dimethyl-terminated peptide from the Bahamian cyanobacterium Symploca sp., were assigned from spectroscopic analysis, including MS, 2D NMR, and Marfey's analysis. The complete absolute configuration of symplocin A, including the unexpected D-configurations of the terminal N,N-dimethylisoleucine and valic acid residues, was assigned by chiral-phase HPLC of the corresponding 2-naphthacyl esters, a highly sensitive, complementary strategy for assignment of N-blocked peptide residues where Marfey's method is ineffectual or other methods fall short. Symplocin A exhibited potent activity as an inhibitor of cathepsin E (IC50 300 pM).

  DOI：

  10.1021/np200861n

文献信息

• Ingram, Journal of Biological Chemistry, 1953, vol. 202, p. 193,194
  作者：Ingram

  DOI：——

  日期：——
• Symplocin A, a Linear Peptide from the Bahamian Cyanobacterium<i>Symploca</i>sp. Configurational Analysis of<i>N</i>,<i>N</i>-Dimethylamino Acids by Chiral-Phase HPLC of Naphthacyl Esters
  作者：Tadeusz F. Molinski、Kirk A. Reynolds、Brandon I. Morinaka

  DOI：10.1021/np200861n

  日期：2012.3.23

  The absolute stereostructures of the components of symplocin A (3), a new N,N-dimethyl-terminated peptide from the Bahamian cyanobacterium Symploca sp., were assigned from spectroscopic analysis, including MS, 2D NMR, and Marfey's analysis. The complete absolute configuration of symplocin A, including the unexpected D-configurations of the terminal N,N-dimethylisoleucine and valic acid residues, was assigned by chiral-phase HPLC of the corresponding 2-naphthacyl esters, a highly sensitive, complementary strategy for assignment of N-blocked peptide residues where Marfey's method is ineffectual or other methods fall short. Symplocin A exhibited potent activity as an inhibitor of cathepsin E (IC50 300 pM).