methyl (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-3-(4-hydroxyphenyl)-2-[[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methylamino]propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoate | 177895-44-2

• 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: methyl (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-3-(4-hydroxyphenyl)-2-[[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methylamino]propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoate
• CAS: 177895-44-2
• 化学式: C₄₁H₅₇N₅O₁₂
• 分子量: 811.93
• InChiKey: IAUIBCRCFWXOGD-TZCOYYEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  58
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  221
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 methyl (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-3-(4-hydroxyphenyl)-2-[[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methylamino]propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoate 以 水 为溶剂， 反应 24.0h， 以60%的产率得到N-(1-deoxy-D-fructos-1-yl)-L-tyrosylglycylglycyl-L-phenylalanyl-L-leucine methyl ester trifluoroacetate
  参考文献：
  名称：

  Synthesis and¹³C NMR investigation of novel Amadori compounds (1-amino-1-deoxy-D-fructose derivatives) related to the opioid peptide, leucine–enkephalin

  摘要：

  The N-(1-deoxy-D-fructos-1-yl) derivatives (Amadori compounds) of the endogenous opioid pentapeptide, leucine-enkephalin (11), leucine-enkephalin methyl ester (12) and of structurally related peptides (9, 10) are synthesized. The equilibrium compositions of the prepared Amadori compounds 9-12 in D2O and [H-2(6)]DMSO are determined using C-13 NMR spectroscopy. In water, the beta-pyranose, a-furanose and beta-furanose forms are detected, the beta-pyranose tautomer being the most abundant at equilibrium (67-75%). The alpha-pyranose form and open-chain keto form are not detected. In dimethyl sulfoxide, the equilibrium compositions of 9-12 are markedly shifted towards a higher proportion of furanose forms, amounting to two-thirds of the mixture. In addition to the alpha- and beta-furanoses and beta-pyranose tautomers, DMSO solutions of compounds 9-12 contain at equilibrium a relatively high proportion of the acyclic hydrate (gem-diol) form (ca. 10%).

  DOI：

  10.1039/p29960000789
• 作为产物：
  描述：

  2-[[2-[[(2S)-3-(4-hydroxyphenyl)-2-[[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methylamino]propanoyl]amino]acetyl]amino]acetic acid 在 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 生成 methyl (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-3-(4-hydroxyphenyl)-2-[[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methylamino]propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoate
  参考文献：
  名称：

  Synthesis and¹³C NMR investigation of novel Amadori compounds (1-amino-1-deoxy-D-fructose derivatives) related to the opioid peptide, leucine–enkephalin

  摘要：

  The N-(1-deoxy-D-fructos-1-yl) derivatives (Amadori compounds) of the endogenous opioid pentapeptide, leucine-enkephalin (11), leucine-enkephalin methyl ester (12) and of structurally related peptides (9, 10) are synthesized. The equilibrium compositions of the prepared Amadori compounds 9-12 in D2O and [H-2(6)]DMSO are determined using C-13 NMR spectroscopy. In water, the beta-pyranose, a-furanose and beta-furanose forms are detected, the beta-pyranose tautomer being the most abundant at equilibrium (67-75%). The alpha-pyranose form and open-chain keto form are not detected. In dimethyl sulfoxide, the equilibrium compositions of 9-12 are markedly shifted towards a higher proportion of furanose forms, amounting to two-thirds of the mixture. In addition to the alpha- and beta-furanoses and beta-pyranose tautomers, DMSO solutions of compounds 9-12 contain at equilibrium a relatively high proportion of the acyclic hydrate (gem-diol) form (ca. 10%).

  DOI：

  10.1039/p29960000789

文献信息

• Synthesis and¹³C NMR investigation of novel Amadori compounds (1-amino-1-deoxy-<scp>D</scp>-fructose derivatives) related to the opioid peptide, leucine–enkephalin
  作者：Andreja Jakas、Štefica Horvat

  DOI：10.1039/p29960000789

  日期：——

  The N-(1-deoxy-D-fructos-1-yl) derivatives (Amadori compounds) of the endogenous opioid pentapeptide, leucine-enkephalin (11), leucine-enkephalin methyl ester (12) and of structurally related peptides (9, 10) are synthesized. The equilibrium compositions of the prepared Amadori compounds 9-12 in D2O and [H-2(6)]DMSO are determined using C-13 NMR spectroscopy. In water, the beta-pyranose, a-furanose and beta-furanose forms are detected, the beta-pyranose tautomer being the most abundant at equilibrium (67-75%). The alpha-pyranose form and open-chain keto form are not detected. In dimethyl sulfoxide, the equilibrium compositions of 9-12 are markedly shifted towards a higher proportion of furanose forms, amounting to two-thirds of the mixture. In addition to the alpha- and beta-furanoses and beta-pyranose tautomers, DMSO solutions of compounds 9-12 contain at equilibrium a relatively high proportion of the acyclic hydrate (gem-diol) form (ca. 10%).