(113C)methyl (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-[3-[[2-[[(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37R,38S)-33-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-38-fluoro-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carbonyl]amino]acetyl]amino]propylamino]-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate | 1401611-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (113C)methyl (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-[3-[[2-[[(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37R,38S)-33-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-38-fluoro-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carbonyl]amino]acetyl]amino]propylamino]-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate
• CAS: 1401611-39-9
• 化学式: C₁₀₀H₁₅₅FN₄O₃₄
• 分子量: 1977.32
• InChiKey: NKMZWMQDVJMPKI-WPLRIDIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  139
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  635
• 氢给体数：
  24
• 氢受体数：
  37

反应信息

• 作为产物：
  描述：

  在 哌啶 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以1.8 mg的产率得到(113C)methyl (1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(2R,3S,4S,5S,6R)-4-[3-[[2-[[(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37R,38S)-33-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-38-fluoro-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carbonyl]amino]acetyl]amino]propylamino]-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylate
  参考文献：
  名称：

  Possible conformation of amphotericin B dimer in membrane-bound assembly as deduced from solid-state NMR

  摘要：

  Aiming for structural analysis of amphotericin B (AmB) ion-channel assemblies in membrane, a covalent dimer was synthesized between C-13-labled AmB methyl ester and F-19-labled AmB. The dimer showed slightly weaker but significant biological activities against fungi and red blood cells compared with those of monomeric AmB. Then the dimer was subjected to C-13{F-19}REDOR (Rotational-Echo Double Resonance) experiments in hydrated lipid bilayers. The obtained REDOR dephasing effects were explained by two components; a short C-13/F-19 distance (6.9 angstrom) accounting for 23% of the REDOR dephasing, and a longer one (14 angstrom) comprising the rest of the dephasing. The shorter distance is likely to reflect the formation of barrel-stave ion channel. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.016