(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methylamino]hexanoic acid | 1133875-57-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methylamino]hexanoic acid
• CAS: 1133875-57-6
• 化学式: C₃₃H₄₂N₂O₉
• 分子量: 610.704
• InChiKey: WUQIYXMXHZSEDV-SQZRHIBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  133.81
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methylamino]hexanoic acid 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以46%的产率得到Nα-9-fluorenylmethoxycarbonyl-Nε-tert-butyloxycarbonyl-Nε-N-(2,3:4,5-di-O-isopropyliden-1-deoxy-β-D-fructopyranose-1-ylo)lysine
  参考文献：
  名称：

  的2,3水合物：4,5-二-O-异亚丙基β- d - 阿拉伯 -hexos -2- ULO -2,6-吡喃糖作为新的结晶试剂在阿马多利的制备衍生的肽

  摘要：

  我们建立，即2,3-结晶水合物：4,5-二-O-异亚丙基β- d - 阿拉伯 -hexos -2- ULO -2,6-吡喃糖是用于固相合成一个新的，方便稳定的试剂肽衍生的Amadori产品。通过X射线分析，NMR光谱和高分辨率ESI-MS研究了标题化合物的结构。晶体结构表明存在两个不与氢键连接的非对称性分子。与先前报道的2,3：4,5-二-O-异亚丙基-β-D-果糖吡喃糖的比较表明，这两种化合物是同构的。

  DOI：

  10.2478/s11532-009-0123-y
• 作为产物：
  描述：

  Fmoc-Lys-OH*TFA 、 2,3:4,5-bis-O-(isopropylidene)-D-fructopyranose aldehyde 在 sodium cyanoborohydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methylamino]hexanoic acid
  参考文献：
  名称：

  Methods of the site-selective solid phase synthesis of peptide-derived Amadori products

  摘要：

  Two procedures of glycated peptides' synthesis have been developed. The first method involves reductive alkylation of the epsilon-amino groups of lysine with 2,3:4,5-di-O-isopropylidene-beta-d-arabino-hexos-2-ulo-2,6-pyranose in the presence of sodium cyanoborohydride on solid support. The second one uses a new fully protected lysine derivative, which is a building block designed for direct introduction of the glycated lysine moiety into a peptide, according to the standard solid phase synthesis protocol. The applicability of the proposed methods for the synthesis of peptide-derived Amadori products is discussed. The structure of the synthesized glycated peptides was confirmed by high-resolution mass spectrometry and enzymatic hydrolysis. Circular dichroism studies, performed in water solution, revealed that the formation of the Amadori rearrangement product in the lysine side chain does not influence significantly the conformational preferences of the peptides studied. However, when the solvent was changed to trifluoroethanol, the glycated peptides preferred beta-turn conformation.

  DOI：

  10.1007/s00726-009-0294-z