Nα-t-Butoxycarbonyl-L-leucyl-α,β-dehydrophenylalanine azolactone | 75186-23-1

• 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: Nα-t-Butoxycarbonyl-L-leucyl-α,β-dehydrophenylalanine azolactone
• 英文别名: N^α-t-Butoxycarbonyl-L-leucyl-α,β-dehydrophenylalanine azolactone
• CAS: 75186-23-1
• 化学式: C₂₀H₂₆N₂O₄
• 分子量: 358.437
• InChiKey: IKUBTNQPSQRTJR-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  76.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  L-色氨酸甲酯盐酸盐 、 Nα-t-Butoxycarbonyl-L-leucyl-α,β-dehydrophenylalanine azolactone 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 200.0h， 以72%的产率得到Boc-L-Leu-(Z)-ΔPhe-L-Trp-OCH3
  参考文献：
  名称：

  Design of peptides with α,β-dehydro-residues: syntheses, crystal structures and molecular conformations of two ΔPhe-Trp containing peptides

  摘要：

  The DeltaPhe-Trp is a newly designed moiety that was found inducing a unique conformation in peptides. The peptides Boc-L-Val-DeltaPhe-L-Trp-OCH3 (I) and Boc-L-Leu-DeltaPhe-L-Trp-OCH3 (II) were synthesized by azlactone method in solution phase. The peptide (I) was crystallized from its solution in ethanol-water mixture in orthorhombic space group P2(1)2(1)2(1) with a = 10.663(3) Angstrom, b = 11.204(3) Angstrom, c = 26.516(10) Angstrom and peptide (II) was crystallized from its solution in acetone in a monoclinic space group P2(1) with a = 9.354(1)Angstrom, b = 11.218(4)Angstrom, c = 15.633(1)Angstrom and beta = 101.83(1). The structures were determined by direct methods. Peptide (I) was refined to an R value of 0.059 for 1554 observed reflections [I greater than or equal to 2sigma (I)] and peptide (II) was refined to an R value of 0.043 for 2920 observed reflections [I greater than or equal to 2sigma (1)]. The structures of peptides (I) and (II) were found to be identical. They formed an unusual type VIa beta-turn conformation which is observed for the first time with a APhe residue at (i + 2) position indicating a unique influence of DeltaPhe-Trp moiety in inducing a reproducible new structure in peptides. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(03)00173-x
• 作为产物：
  描述：

  Boc-L-Leu-DL-(β-OH)-Phe-OH 在 sodium acetate 、 乙酸酐 作用下， 反应 96.0h， 以80%的产率得到Nα-t-Butoxycarbonyl-L-leucyl-α,β-dehydrophenylalanine azolactone
  参考文献：
  名称：

  Design of peptides with α,β-dehydro-residues: syntheses, crystal structures and molecular conformations of two ΔPhe-Trp containing peptides

  摘要：

  The DeltaPhe-Trp is a newly designed moiety that was found inducing a unique conformation in peptides. The peptides Boc-L-Val-DeltaPhe-L-Trp-OCH3 (I) and Boc-L-Leu-DeltaPhe-L-Trp-OCH3 (II) were synthesized by azlactone method in solution phase. The peptide (I) was crystallized from its solution in ethanol-water mixture in orthorhombic space group P2(1)2(1)2(1) with a = 10.663(3) Angstrom, b = 11.204(3) Angstrom, c = 26.516(10) Angstrom and peptide (II) was crystallized from its solution in acetone in a monoclinic space group P2(1) with a = 9.354(1)Angstrom, b = 11.218(4)Angstrom, c = 15.633(1)Angstrom and beta = 101.83(1). The structures were determined by direct methods. Peptide (I) was refined to an R value of 0.059 for 1554 observed reflections [I greater than or equal to 2sigma (I)] and peptide (II) was refined to an R value of 0.043 for 2920 observed reflections [I greater than or equal to 2sigma (1)]. The structures of peptides (I) and (II) were found to be identical. They formed an unusual type VIa beta-turn conformation which is observed for the first time with a APhe residue at (i + 2) position indicating a unique influence of DeltaPhe-Trp moiety in inducing a reproducible new structure in peptides. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(03)00173-x

文献信息

• Solution conformation and synthesis of a linear heptapeptide containing two dehydrophenylalanine residues separated by three L-amino acids
  作者：Alka Gupta、Ashima Bharadwaj、Virander S. Chauhan

  DOI：10.1039/p29900001911

  日期：——

  A heptapeptide containing two dehydrophenylalanine residues, Boc-Gly-ΔzPhe-Ala-Phe-Leu-ΔzPhe-Ala-NHMe (Boc = t-butoxycarbonyl) has been synthesised and its solution conformation investigated using 500 MHz 1H NMR and IR spectroscopy. 1H NMR studies of the solvent accessibility of NH resonances and observation of successive Ni,H ↔ Ni+1H nuclear Overhauser effects (NOEs) suggest the presence of a significant

  甲含有两个dehydrophenyLALAnine残基七肽，将Boc-甘氨酸- Δ Ž的Phe-丙氨酸-苯丙氨酸-亮氨酸- Δ Ž的Phe-ALA-NHMe（Boc =叔丁氧羰基）已被合成，并且其溶液构象使用500兆赫研究1 H NMR和红外光谱。NH共振的溶剂可及性的1 H NMR研究以及连续的N i，H↔N i +1 H核Overhauser效应（NOEs）的观察表明，CDCl 3中存在大量折叠的螺旋结构。5→1分子内氢键模式提供了有利于α-螺旋构象的证据。在（CD 3）2所以，尽管所述肽在很大程度上有利于螺旋构象，几的C观察我α ħ↔Ñ我1层ħ的NOE给出了一些构象异质性的指示。氯仿中的IR研究提供了支持这些结论的支持证据。脱氢苯丙氨酸残基在设计具有优选二级结构的肽中可能具有潜在用途。