N6-[2-(2-呋喃基)-2-氧代乙基]-L-赖氨酸 | 19746-33-9

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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
• 中文名称: N6-[2-(2-呋喃基)-2-氧代乙基]-L-赖氨酸
• 英文名称: furosine
• 英文别名: (2S)-2-amino-6-[[2-(furan-2-yl)-2-oxoethyl]amino]hexanoic acid
• CAS: 19746-33-9
• 化学式: C₁₂H₁₈N₂O₄
• 分子量: 254.286
• InChiKey: YQHPCDPFXQXCMV-VIFPVBQESA-N

物化性质

• 沸点：
  462.7±45.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N6-[2-(2-呋喃基)-2-氧代乙基]-L-赖氨酸 、 水 、 盐酸 生成 L-赖氨酸
  参考文献：
  名称：

  SZOLGYENYI, GERALD P.;WINSAUER, KARL J. B.;DEUTSCH, ERWIN, MONATSH. CHEM., 120,(1989) N2, C. 1147-1158

  摘要：

  DOI：
• 作为产物：
  描述：

  果糖基-赖氨酸 在 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 N6-[2-(2-呋喃基)-2-氧代乙基]-L-赖氨酸
  参考文献：
  名称：

  Glucoselysine is derived from fructose and accumulates in the eye lens of diabetic rats

  摘要：

  Prolonged hyperglycemia generates advanced glycation end-products (AGEs), which are believed to be involved in the pathogenesis of diabetic complications. In the present study, we developed a polyclonal antibody against fructose-modified proteins (Fru-P antibody) and identified its epitope as glucoselysine (GL) by NMR and LC-electrospray ionization (ESI)-quadrupole TOF (QTOF) analyses and evaluated its potential role in diabetes sequelae. Although the molecular weight of GL was identical to that of fructoselysine (FL), GL was distinguishable from FL because GL was resistant to acid hydrolysis, which converted all of the FLs to furosine. We also detected GL in vitro when reduced BSA was incubated with fructose for 1 day. However, when we incubated reduced BSA with glucose, galactose, or mannose for 14 days, we did not detect GL, suggesting that GL is dominantly generated from fructose. LC-ESI-MS/MS experiments with synthesized [C-13(6)]GL indicated that the GL levels in the rat eye lens time-dependently increase after streptozotocin-induced diabetes. We observed a 31.3-fold increase in GL 8 weeks after the induction compared with nondiabetic rats, and N epsilon-(carboxymethyl)lysine and furosine increased by 1.7- and 21.5-fold, respectively, under the same condition. In contrast, sorbitol in the lens levelled off at 2 weeks after diabetes induction. We conclude that GL may be a useful biological marker to monitor and elucidate the mechanism of protein degeneration during progression of diabetes.

  DOI：

  10.1074/jbc.ra119.010744

文献信息

• Studies on N-Terminal Glycation of Peptides in Hypoallergenic Infant Formulas:  Quantification of α-<i>N</i>-(2-Furoylmethyl) Amino Acids
  作者：Ilka Penndorf、Daniela Biedermann、Sarah V. Maurer、Thomas Henle

  DOI：10.1021/jf061821b

  日期：2007.2.1

  To obtain information about the extent of the early Maillard reaction between the N-termini of peptides and lactose, alpha-N-(2-furoylmethyl) amino acids (FMAAs) were quantified together with is an element of-N-(2-furoylmethyl) lysine (furosine) in acid hydrolyzates of hypoallergenic infant formulas, conventional infant formulas, and human milk samples using RP-HPLC with UV-detection. FMAAs are formed during acid hydrolysis of peptide-bound N-terminal Amadori products (APs), and furosine is formed from the Amadori products of peptide-bound lysine. Unambiguous identification was achieved by means of LC/MS and UV-spectroscopy using independently prepared reference material. The extent of acid-induced conversion of APs to FMAAs was studied by RP-HPLC with chemiluminescent nitrogen detection (CLND). Depending on the corresponding alpha-N-lactulosyl amino acid, between 6.0% and 18.1% of FMAAs were formed during hydrolysis for 23 h at 110 degrees C in 8 N HCl. From is an element of-N-lactulosyllysine, 50% furosine is formed under these conditions. Whereas furosine was detectable in all assayed samples, five different FMAAs, alpha-FM-Lys, alpha-FM-Ala, alpha-FM-Val, alpha-FM-Ile, and alpha-FM-Leu, were exclusively detected in acid hydrolyzates of hypoallergenic infant formulas in amounts ranging from 35 to 396 mu mol/100 g protein. Taking the conversion factors into account, modification of N-terminal amino acids in peptides by reducing carbohydrates was between 0.3% and 8.4%. This has to be considered within the discussion concerning the nutritional quality of peptide- containing foods.
• Glucoselysine is derived from fructose and accumulates in the eye lens of diabetic rats
  作者：Rei-ichi Ohno、Kenta Ichimaru、Seitaro Tanaka、Hikari Sugawa、Nana Katsuta、Shiori Sakake、Yu-ki Tominaga、Ikuho Ban、Jun-ichi Shirakawa、Yoshiki Yamaguchi、Emi Ito、Naoyuki Taniguchi、Ryoji Nagai

  DOI：10.1074/jbc.ra119.010744

  日期：2019.11

  Prolonged hyperglycemia generates advanced glycation end-products (AGEs), which are believed to be involved in the pathogenesis of diabetic complications. In the present study, we developed a polyclonal antibody against fructose-modified proteins (Fru-P antibody) and identified its epitope as glucoselysine (GL) by NMR and LC-electrospray ionization (ESI)-quadrupole TOF (QTOF) analyses and evaluated its potential role in diabetes sequelae. Although the molecular weight of GL was identical to that of fructoselysine (FL), GL was distinguishable from FL because GL was resistant to acid hydrolysis, which converted all of the FLs to furosine. We also detected GL in vitro when reduced BSA was incubated with fructose for 1 day. However, when we incubated reduced BSA with glucose, galactose, or mannose for 14 days, we did not detect GL, suggesting that GL is dominantly generated from fructose. LC-ESI-MS/MS experiments with synthesized [C-13(6)]GL indicated that the GL levels in the rat eye lens time-dependently increase after streptozotocin-induced diabetes. We observed a 31.3-fold increase in GL 8 weeks after the induction compared with nondiabetic rats, and N epsilon-(carboxymethyl)lysine and furosine increased by 1.7- and 21.5-fold, respectively, under the same condition. In contrast, sorbitol in the lens levelled off at 2 weeks after diabetes induction. We conclude that GL may be a useful biological marker to monitor and elucidate the mechanism of protein degeneration during progression of diabetes.
• SZOLGYENYI, GERALD P.;WINSAUER, KARL J. B.;DEUTSCH, ERWIN, MONATSH. CHEM., 120,(1989) N2, C. 1147-1158
  作者：SZOLGYENYI, GERALD P.、WINSAUER, KARL J. B.、DEUTSCH, ERWIN

  DOI：——

  日期：——