N^α,N^ε-di-(1-deoxy-α,β-D-fructofuranos-1-yluronic acid)-L-lysyl-glycyl-glycyl-L-phenylalanyl-L-leucine | 1217317-38-8

• 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^α,N^ε-di-(1-deoxy-α,β-D-fructofuranos-1-yluronic acid)-L-lysyl-glycyl-glycyl-L-phenylalanyl-L-leucine
• 英文别名: (2S,3S,4S)-5-[[[(5S)-6-[[2-[[2-[[(2S)-1-[[(1S)-1-carboxy-3-methylbutyl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-2-oxoethyl]amino]-2-oxoethyl]amino]-5-[[(3S,4S,5S)-5-carboxy-2,3,4-trihydroxyoxolan-2-yl]methylamino]-6-oxohexyl]amino]methyl]-3,4,5-trihydroxyoxolane-2-carboxylic acid
• CAS: 1217317-38-8
• 化学式: C₃₇H₅₆N₆O₁₈
• 分子量: 872.881
• InChiKey: DPVOINKBYXQKLU-GKCVBWSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.6
• 重原子数：
  61
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  392
• 氢给体数：
  15
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  D-吡喃葡萄糖醛酸 、 Lys-Gly-Gly-Phe-Leu diacetate 以 甲醇 为溶剂， 反应 72.0h， 以15%的产率得到N^ε-(1-deoxy-α,β-D-fructofuranos-1-yluronic acid)-L-lysyl-glycyl-glycyl-L-phenylalanyl-L-leucine
  参考文献：
  名称：

  Glycosylation of lysine-containing pentapeptides by glucuronic acid: new insights into the Maillard reaction

  摘要：

  The formation of glycosylation products in model systems consisting Of D-glucuronic acid (GlcA) and lysine-containing peptides, such as Lys-Gly-Gly-Phe-Leu (1), Gly-Lys-Gly-Phe-Leu (4) and Ac-Gly-Lys-Gly-Phe-Leu (6), was examined to evaluate the site specificity as well as the extent and nature of the modification. Peptides were reacted with GlcA either in solution or under dry-heating conditions. From the incubations performed in solution (MeOH), the corresponding (1-deoxy-D-fructofuranos-1-yluronic acid)-peptide derivatives (Amadori compounds) were isolated. Whereas reaction of 1 resulted in the formation of mono-glycosylated Amadori compound 2 with the sugar moiety attached to the N(epsilon)-amino group of the Lys residue and its di-glycosylated analogue 3, exposure of 4 to GlcA afforded only di-glycosylated peptide 5. From the incubation of GlcA with Ac-Gly-Lys-Gly-Phe-Leu (6) performed under mild dry-heating conditions (50 degrees C) in an environment of 75% relative humidity, besides Amadori compound 7, two new Maillard reaction products were isolated that contained 3-hydroxypyridinium (8) and 3-hydroxy-picolinic acid moiety (9). The mechanism for the formation of pyridinium products is discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.11.031

文献信息

• Glycosylation of lysine-containing pentapeptides by glucuronic acid: new insights into the Maillard reaction
  作者：Štefica Horvat、Maja Roščić

  DOI：10.1016/j.carres.2009.11.031

  日期：2010.2

  The formation of glycosylation products in model systems consisting Of D-glucuronic acid (GlcA) and lysine-containing peptides, such as Lys-Gly-Gly-Phe-Leu (1), Gly-Lys-Gly-Phe-Leu (4) and Ac-Gly-Lys-Gly-Phe-Leu (6), was examined to evaluate the site specificity as well as the extent and nature of the modification. Peptides were reacted with GlcA either in solution or under dry-heating conditions. From the incubations performed in solution (MeOH), the corresponding (1-deoxy-D-fructofuranos-1-yluronic acid)-peptide derivatives (Amadori compounds) were isolated. Whereas reaction of 1 resulted in the formation of mono-glycosylated Amadori compound 2 with the sugar moiety attached to the N(epsilon)-amino group of the Lys residue and its di-glycosylated analogue 3, exposure of 4 to GlcA afforded only di-glycosylated peptide 5. From the incubation of GlcA with Ac-Gly-Lys-Gly-Phe-Leu (6) performed under mild dry-heating conditions (50 degrees C) in an environment of 75% relative humidity, besides Amadori compound 7, two new Maillard reaction products were isolated that contained 3-hydroxypyridinium (8) and 3-hydroxy-picolinic acid moiety (9). The mechanism for the formation of pyridinium products is discussed. (C) 2009 Elsevier Ltd. All rights reserved.