[2-(2-tert-Butoxycarbonylamino-acetylamino)-2-propyl-pentanoylamino]-acetic acid benzyl ester | 198288-31-2

• 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: [2-(2-tert-Butoxycarbonylamino-acetylamino)-2-propyl-pentanoylamino]-acetic acid benzyl ester
• CAS: 198288-31-2
• 化学式: C₂₄H₃₇N₃O₆
• 分子量: 463.574
• InChiKey: FLFSURWNLIPTOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  33.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  122.83
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [2-(2-tert-Butoxycarbonylamino-acetylamino)-2-propyl-pentanoylamino]-acetic acid benzyl ester 在 甲酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 130.0h， 生成 [2-(2-{2-[2-(2-tert-Butoxycarbonylamino-acetylamino)-2-propyl-pentanoylamino]-acetylamino}-acetylamino)-2-propyl-pentanoylamino]-acetic acid benzyl ester
  参考文献：
  名称：

  Stereochemical Analysis of Higher α,α-Dialkylglycine Containing Peptides. Characterization of Local Helical Conformations at Dipropylglycine Residues and Observation of a Novel Hydrated Multiple β-Turn Structure in Crystals of a Glycine Rich Peptide

  摘要：

  The peptide Boc-Gly-Dpg-Gly-Gly-Dpg-Gly-NHMe (1) has been synthesized to examine the conformational preferences of Dpg residues in the context of a poor helix promoting sequence. Single crystals of 1 were obtained in the space group P2(1)/c with a = 13.716(2) Angstrom, b = 12.960(2) Angstrom, c = 22.266(4) Angstrom, and beta = 98.05(1)degrees; R = 6.3% for 3660 data with \F-0\ > 4 sigma. The molecular conformation in crystals revealed that the Gly(1)-Dpg(2) segment adopts phi, psi values distorted from those expected for an ideal type II' beta-turn (phi(Gly(1)) = +72.0 degrees, psi(Gly(1)) = -166.0 degrees; phi(Dpg(2)) = -54.0 degrees, psi(Dpg(2)) = -46.0 degrees) with an inserted water molecule between Boc-CO and Gly(3)NH. The Gly(3)-Gly(4) segment adopts phi, psi values which lie broadly in the right handed helical region (phi(Gly(3)) = -78.0 degrees, psi(Gly(3)) = -9.0 degrees; phi(Gly(4)) = -80.0 degrees, psi(Gly(4)) = 18.0 degrees). There is a chiral reversal at Dpg(5) which takes up phi, psi values in the left handed helical region. The Dpg(5)-Gly(6) segment closely resembles an ideal type I' beta-turn (phi(Dpg(5)) = +56.0 degrees, psi(Dpg(5)) = +32.0 degrees; phi(Gly(6)) = +85.0 degrees, psi(Gly(6)) = -3.0 degrees). Molecules of both chiral senses are found in the centrosymmetric crystal. The C-terminus forms a hydrated Schellman motif, with water insertion into the potential 6 --> 1 hydrogen bond between Gly(1)CO and Gly(6)NH. NMR studies in CDCl3 suggest substantial retention of the multiple turn conformation observed in crystals. In solution the observed NOEs support local helical conformation at the two Dpg residues.

  DOI：

  10.1021/ja970596z
• 作为产物：
  描述：

  Methyl 2-amino-2-propylpentanoate 在 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 生成 [2-(2-tert-Butoxycarbonylamino-acetylamino)-2-propyl-pentanoylamino]-acetic acid benzyl ester
  参考文献：
  名称：

  Stereochemical Analysis of Higher α,α-Dialkylglycine Containing Peptides. Characterization of Local Helical Conformations at Dipropylglycine Residues and Observation of a Novel Hydrated Multiple β-Turn Structure in Crystals of a Glycine Rich Peptide

  摘要：

  The peptide Boc-Gly-Dpg-Gly-Gly-Dpg-Gly-NHMe (1) has been synthesized to examine the conformational preferences of Dpg residues in the context of a poor helix promoting sequence. Single crystals of 1 were obtained in the space group P2(1)/c with a = 13.716(2) Angstrom, b = 12.960(2) Angstrom, c = 22.266(4) Angstrom, and beta = 98.05(1)degrees; R = 6.3% for 3660 data with \F-0\ > 4 sigma. The molecular conformation in crystals revealed that the Gly(1)-Dpg(2) segment adopts phi, psi values distorted from those expected for an ideal type II' beta-turn (phi(Gly(1)) = +72.0 degrees, psi(Gly(1)) = -166.0 degrees; phi(Dpg(2)) = -54.0 degrees, psi(Dpg(2)) = -46.0 degrees) with an inserted water molecule between Boc-CO and Gly(3)NH. The Gly(3)-Gly(4) segment adopts phi, psi values which lie broadly in the right handed helical region (phi(Gly(3)) = -78.0 degrees, psi(Gly(3)) = -9.0 degrees; phi(Gly(4)) = -80.0 degrees, psi(Gly(4)) = 18.0 degrees). There is a chiral reversal at Dpg(5) which takes up phi, psi values in the left handed helical region. The Dpg(5)-Gly(6) segment closely resembles an ideal type I' beta-turn (phi(Dpg(5)) = +56.0 degrees, psi(Dpg(5)) = +32.0 degrees; phi(Gly(6)) = +85.0 degrees, psi(Gly(6)) = -3.0 degrees). Molecules of both chiral senses are found in the centrosymmetric crystal. The C-terminus forms a hydrated Schellman motif, with water insertion into the potential 6 --> 1 hydrogen bond between Gly(1)CO and Gly(6)NH. NMR studies in CDCl3 suggest substantial retention of the multiple turn conformation observed in crystals. In solution the observed NOEs support local helical conformation at the two Dpg residues.

  DOI：

  10.1021/ja970596z