H-Tyr(β-D-Lac)-Gly-Ala-NH2

• 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: H-Tyr(β-D-Lac)-Gly-Ala-NH2
• 英文别名: (2S)-2-amino-N-[2-[[(2S)-1-amino-1-oxopropan-2-yl]amino]-2-oxoethyl]-3-[4-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxyphenyl]propanamide
• 化学式: C₂₆H₄₀N₄O₁₄
• 分子量: 632.622
• InChiKey: OGQPXRUEXVQJEO-QGXCFLFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  306
• 氢给体数：
  11
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 H-Tyr(β-D-Lac)-Gly-Ala-NH2
  参考文献：
  名称：

  Convenient high yield and stereoselective synthesis of O -glycopeptides using N -α-Fmoc-Tyr/Ser[β- d -Glc(OAc) 4 ]OPfp generated in solution

  摘要：

  Fmoc-AA-OPfp (AA = Tyr or Ser) (1 equiv) was reacted with beta-D-Glc(OAc)(5) (6 equiv) in the presence of BF3.Et2O (6 equiv) in CH2Cl2 at room temperature for 2 h, and the glycosylation reaction mixture was used directly to couple to the amino group of the peptide resin without isolation and purification of the Fmoc-AA[beta-D-Glc(OAc)(4)]-OPfp. Moreover, the -OAc protecting groups of glucose was removed just prior to releasing the peptide from the resin using 6 mM NaOMe in 85% DMF-MeOH. The crude product obtained by TEA cleavage contained >90%, of the target O-glycopeptide, and the 500 MHz H-1 NMR analysis revealed that the glycosylation reaction was nearly stereoselective (>97% beta-anomer). This method is rapid and stereoselective, and can now be exploited for the routine synthesis of O-glycopeptides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.178

文献信息

• Convenient high yield and stereoselective synthesis of O -glycopeptides using N -α-Fmoc-Tyr/Ser[β- d -Glc(OAc) 4 ]OPfp generated in solution
  作者：Beechanahalli P. Gangadhar、Seetharama D.S. Jois、Ambikaipakan Balasubramaniam

  DOI：10.1016/j.tetlet.2003.10.178

  日期：2004.1

  Fmoc-AA-OPfp (AA = Tyr or Ser) (1 equiv) was reacted with beta-D-Glc(OAc)(5) (6 equiv) in the presence of BF3.Et2O (6 equiv) in CH2Cl2 at room temperature for 2 h, and the glycosylation reaction mixture was used directly to couple to the amino group of the peptide resin without isolation and purification of the Fmoc-AA[beta-D-Glc(OAc)(4)]-OPfp. Moreover, the -OAc protecting groups of glucose was removed just prior to releasing the peptide from the resin using 6 mM NaOMe in 85% DMF-MeOH. The crude product obtained by TEA cleavage contained >90%, of the target O-glycopeptide, and the 500 MHz H-1 NMR analysis revealed that the glycosylation reaction was nearly stereoselective (>97% beta-anomer). This method is rapid and stereoselective, and can now be exploited for the routine synthesis of O-glycopeptides. (C) 2003 Elsevier Ltd. All rights reserved.