Nα-9-fluorenylmethoxycarbonyl-Nε-tert-butoxycarbonyl-L-lysyl-L-leucyl-L-glycine tert-butyl ester | 253584-96-2

• 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: Nα-9-fluorenylmethoxycarbonyl-Nε-tert-butoxycarbonyl-L-lysyl-L-leucyl-L-glycine tert-butyl ester
• 英文别名: N_α-9-fluorenylmethoxycarbonyl-N_ε-tert-butoxycarbonyl-L-lysyl-L-leucyl-L-glycine tert-butyl ester
• CAS: 253584-96-2
• 化学式: C₃₈H₅₄N₄O₈
• 分子量: 694.869
• InChiKey: NXJUEDYDIHMNNL-CONSDPRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  50.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  161.16
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Nα-9-fluorenylmethoxycarbonyl-Nε-tert-butoxycarbonyl-L-lysyl-L-leucyl-L-glycine tert-butyl ester 在 吗啉 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 Nα-9-fluorenylmethoxycarbonyl-L-alanyl-Nε-tert-butoxycarbonyl-L-lysyl-L-leucyl-L-glycine tert-butyl ester
  参考文献：
  名称：

  Development of a Stable Isotope Dilution Assay for an Accurate Quantification of Protein-Bound N_ε-(1-Deoxy-d-fructos-1-yl)-l-lysine Using a ¹³C-Labeled Internal Standard

  摘要：

  Syntheses of the labeled Amadori compound [C-13(6)]-N-epsilon-(1-deoxy-D-fructos-1-yl)-L-lysine ([C-13(6)]-DFLys) and the labeled glycated tetrapeptide Ala-[C-13(6)]-DFLys-Leu-Gly are presented. The compounds were used in the development of stable isotope dilution assays for the quantification of the degree of glycosylation of bovine serum albumin treated for 20 min at 95 degrees C in the presence of glucose. The experiments revealed that the use of the labeled standards in combination with LC/MS allowed the exact quantification of protein-bound DFLys with the high recovery rate of 95% (at a spike level of 150 nmol/mg of protein) and a low detection limit of 5 nmol/mg of protein. The data revealed, however, that DFLys is significantly degraded during the enzymic hydrolysis of the protein backbone generally needed in the quantification procedure and, furthermore, incomplete digestion of the protein was observed. Both sources of errors were clearly overcome by using in particular the labeled peptide as the internal standard.

  DOI：

  10.1021/jf9904315
• 作为产物：
  描述：

  甘氨酸叔丁酯盐酸盐 、 N_α-9-fluorenylmethoxycarbonyl-N_ε-tert-butoxycarbonyl-L-lysyl-L-leucine hydrochloride 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 以90%的产率得到Nα-9-fluorenylmethoxycarbonyl-Nε-tert-butoxycarbonyl-L-lysyl-L-leucyl-L-glycine tert-butyl ester
  参考文献：
  名称：

  Development of a Stable Isotope Dilution Assay for an Accurate Quantification of Protein-Bound N_ε-(1-Deoxy-d-fructos-1-yl)-l-lysine Using a ¹³C-Labeled Internal Standard

  摘要：

  Syntheses of the labeled Amadori compound [C-13(6)]-N-epsilon-(1-deoxy-D-fructos-1-yl)-L-lysine ([C-13(6)]-DFLys) and the labeled glycated tetrapeptide Ala-[C-13(6)]-DFLys-Leu-Gly are presented. The compounds were used in the development of stable isotope dilution assays for the quantification of the degree of glycosylation of bovine serum albumin treated for 20 min at 95 degrees C in the presence of glucose. The experiments revealed that the use of the labeled standards in combination with LC/MS allowed the exact quantification of protein-bound DFLys with the high recovery rate of 95% (at a spike level of 150 nmol/mg of protein) and a low detection limit of 5 nmol/mg of protein. The data revealed, however, that DFLys is significantly degraded during the enzymic hydrolysis of the protein backbone generally needed in the quantification procedure and, furthermore, incomplete digestion of the protein was observed. Both sources of errors were clearly overcome by using in particular the labeled peptide as the internal standard.

  DOI：

  10.1021/jf9904315