2-phenylethyl [6-O-(2-glycylaminoethyl phosphonato)-α-D-mannopyranosyl]-(1->2)-(α-D-mannopyranosyl)-(1->6)-α-D-mannopyranoside | 1208120-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-phenylethyl [6-O-(2-glycylaminoethyl phosphonato)-α-D-mannopyranosyl]-(1->2)-(α-D-mannopyranosyl)-(1->6)-α-D-mannopyranoside
• CAS: 1208120-30-2
• 化学式: C₃₀H₄₉N₂O₂₀P
• 分子量: 788.694
• InChiKey: SLRXNEQXWNPJRR-MHILTJTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.09
• 重原子数：
  53.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  348.33
• 氢给体数：
  12.0
• 氢受体数：
  20.0

反应信息

• 作为产物：
  描述：

  triethylammonium 2-phenylethyl {2,3,4-tri-O-benzyl-6-O-[2-((N-benzyloxycarbonylglycyl)amino)ethylphosphonato]-α-D-mannopyranosyl}-(1->2)-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 48.0h， 以75%的产率得到2-phenylethyl [6-O-(2-glycylaminoethyl phosphonato)-α-D-mannopyranosyl]-(1->2)-(α-D-mannopyranosyl)-(1->6)-α-D-mannopyranoside
  参考文献：
  名称：

  Sortase A-Catalyzed Transpeptidation of Glycosylphosphatidylinositol Derivatives for Chemoenzymatic Synthesis of GPI-Anchored Proteins

  摘要：

  Several peptides/small proteins and glycosylphosphatidylinositol (GPI) derivatives were synthesized and compared as substrates of sortase A (SrtA), a bacterial transpeptidase, for enzymatic coupling. It was observed that peptides containing the LPKTGGS and LPKTGGRS sequences as sorting signals at the peptide C-terminus were effectively coupled to GPI derivatives having one or two glycine residues attached to the phosphoethanolamine group at the nonreducing end. This reaction was employed to prepare several analogues of the human CD52 and CD24 antigens, which are naturally GPI-anchored glycopeptides/glycoproteins. It was further observed that the trisaccharide GPI analogues 5 and 6 were better SrtA substrates than monosaccharide GPI analogue 4, suggesting that steric hindrance of the GPI analogues does not affect their peptidation reaction mediated by SrtA. Therefore, this synthetic strategy may be useful for the preparation of more complex GPI-anchored peptides, glycopeptides, proteins, and glycoproteins.

  DOI：

  10.1021/ja906611x