N-(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl)-L-leucyl-L-seryl-N^ε-(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl)-L-lysyl-L-leucine | 1072134-63-4

• 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: N-(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl)-L-leucyl-L-seryl-N^ε-(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl)-L-lysyl-L-leucine
• 英文别名: (2S)-2-[[(2S)-2-[[(2S)-3-hydroxy-2-[[(2S)-4-methyl-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]pentanoyl]amino]propanoyl]amino]-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]hexanoyl]amino]-4-methylpentanoic acid
• CAS: 1072134-63-4
• 化学式: C₄₅H₇₇N₅O₁₆
• 分子量: 944.13
• InChiKey: TYUVOYHJNSYJLU-KLZJWFKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  66
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  261
• 氢给体数：
  7
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  N-(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl)-L-leucyl-L-seryl-N^ε-(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl)-L-lysyl-L-leucine 、 三氟乙酸 在 苯甲醚 作用下， 以 水 为溶剂， 反应 0.5h， 以40%的产率得到N-(1-deoxy-D-fructos-1-yl)-L-leucyl-L-seryl-N^ε-(1-deoxy-D-fructos-1-yl)-L-lysyl-L-leucine TFA salt
  参考文献：
  名称：

  Glycation of a lysine-containing tetrapeptide by d-glucose and d-fructose—influence of different reaction conditions on the formation of Amadori/Heyns products

  摘要：

  The site specificity, extent, and nature of modification of the tetrapeptide, Leu-Ser-Lys-Leu (1), incubated with D-glucose or D-fructose in methanol, or in phosphate buffer of pH 5.7, 7.4, and 8.0 were investigated. The generated mono- and di-glycated Amadori (1-deoxy-D-fructosyl derivatives) and Heyns rearrangement products (N-alkylated glucosamine/mannosamine derivatives) were isolated and characterized by NMR and mass spectrometry. The results identified the epsilon-amino group of the Lys residue as the preferential glycation site in tetrapeptide 1. Under all conditions investigated, glucose afforded higher yields of glycation products than fructose. In the reactions carried out in buffer, glycation at pH 7.4 and 8.0 was much faster than at pH 5.7. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.07.003
• 作为产物：
  描述：

  2,3:4,5-bis-O-(isopropylidene)-D-fructopyranose aldehyde 、 L-亮氨酰-L-丝氨酰-L-赖氨酰-L-亮氨酸 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以58%的产率得到N-(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl)-L-leucyl-L-seryl-N^ε-(1-deoxy-2,3:4,5-di-O-isopropylidene-β-D-fructopyranos-1-yl)-L-lysyl-L-leucine
  参考文献：
  名称：

  Glycation of a lysine-containing tetrapeptide by d-glucose and d-fructose—influence of different reaction conditions on the formation of Amadori/Heyns products

  摘要：

  The site specificity, extent, and nature of modification of the tetrapeptide, Leu-Ser-Lys-Leu (1), incubated with D-glucose or D-fructose in methanol, or in phosphate buffer of pH 5.7, 7.4, and 8.0 were investigated. The generated mono- and di-glycated Amadori (1-deoxy-D-fructosyl derivatives) and Heyns rearrangement products (N-alkylated glucosamine/mannosamine derivatives) were isolated and characterized by NMR and mass spectrometry. The results identified the epsilon-amino group of the Lys residue as the preferential glycation site in tetrapeptide 1. Under all conditions investigated, glucose afforded higher yields of glycation products than fructose. In the reactions carried out in buffer, glycation at pH 7.4 and 8.0 was much faster than at pH 5.7. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.07.003