(E,E)-N-(tert-butoxycarbonyl)glycyl-α,β-phenylalanylglycyl-α,β-phenylalanylglycine methyl ester | 1092460-06-4

• 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: (E,E)-N-(tert-butoxycarbonyl)glycyl-α,β-phenylalanylglycyl-α,β-phenylalanylglycine methyl ester
• 英文别名: Boc0-Gly1-ΔEPhe2-Gly3-ΔEPhe4-Gly5-OMe
• CAS: 1092460-06-4
• 化学式: C₃₀H₃₅N₅O₈
• 分子量: 593.637
• InChiKey: MUBOBFOSGJWEHT-QAOSGDJLSA-N

反应信息

• 作为反应物：
  描述：

  (E,E)-N-(tert-butoxycarbonyl)glycyl-α,β-phenylalanylglycyl-α,β-phenylalanylglycine methyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以94%的产率得到(E,E)-N-(tert-butoxycarbonyl)glycyl-α,β-phenylalanylglycyl-α,β-phenylalanylglycine
  参考文献：
  名称：

  Two pentadehydropeptides with different configurations of the ΔPhe residues

  摘要：

  Comparison of the crystal structures of two pentadehydropeptides containing Delta Phe residues, namely (Z,Z)-N-(tert-butoxycarbonyl)glycyl-alpha,beta-phenylalanylglycyl-alpha,beta-phenylalanyl-glycine (or Boc(0)-Gly(1)-Delta(Z)Phe(2)-Gly(3)-Delta(Z)Phe(4)-Gly(5)-OH) methanol solvate, C(29)H(33)N(5)O(8)center dot CH(4)O, (I), and (E,E)-N-(tert-butoxycarbonyl)glycyl-alpha,beta-phenylalanylglycyl-alpha,beta-phenylalanylglycine (or Boc(0)-Gly(1)-Delta(E)Phe(2)-Gly(3)-Delta(E)Phe(4)-Gly(5)OH), C(29)H(33)N(5)O(8), (II), indicates that the Delta(Z)Phe residue is a more effective inducer of folded structures than the Delta(E)Phe residue. The values of the torsion angles phi and psi show the presence of two type-III' beta-turns at the Delta(Z)Phe residues and one type-II beta-turn at the Delta(E)Phe residue. All amino acids are linked trans to each other in both peptides. beta-Turns present in the peptides are stabilized by intramolecular 4 -> 1 hydrogen bonds. Molecules in both structures form two-dimensional hydrogen-bond networks parallel to the (100) plane.

  DOI：

  10.1107/s0108270110003094