N-<(Benzyloxy)carbonyl>-4-iodo-L-phenylalanine (trimethylsilyl)ethyl ether | 158686-44-3

• 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: N-<(Benzyloxy)carbonyl>-4-iodo-L-phenylalanine (trimethylsilyl)ethyl ether
• 英文别名: N-[(benzyloxy)carbonyl]-4-iodo-L-phenylalanine (2-trimethylsilyl)ethyl ester；2-trimethylsilylethyl (2S)-3-(4-iodophenyl)-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 158686-44-3
• 化学式: C₂₂H₂₈INO₄Si
• 分子量: 525.459
• InChiKey: YHBUEQXFRMSFLE-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<(Benzyloxy)carbonyl>-4-iodo-L-phenylalanine (trimethylsilyl)ethyl ether 在 四(三苯基膦)钯 四丁基氟化铵 、 methyloxirane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.5h， 生成 (2S)-3-[4-[methoxy-[4-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]phenyl]phosphoryl]phenyl]-2-(phenylmethoxycarbonylamino)propanoic acid
  参考文献：
  名称：

  Efficient Synthesis of a Phosphinate Bis-Amino Acid and Its Use in the Construction of Amphiphilic Peptides

  摘要：

  A new amphiphilic bis-amino acid has been designed and its convergent, asymmetric synthesis achieved in differentially protected form. A convenient preparation of iodophenylalanine, a generally useful starting material, is disclosed. Sequential palladium-catalyzed couplings of aryl iodides to phosphinate lead directly to the target protected bis-amino acid. Controlled peptide coupling of the new bis-amino acid is also demonstrated.

  DOI：

  10.1021/jo00094a036
• 作为产物：
  描述：

  4-iodo-L-phenylalanine 在 吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 N-<(Benzyloxy)carbonyl>-4-iodo-L-phenylalanine (trimethylsilyl)ethyl ether
  参考文献：
  名称：

  Efficient Synthesis of a Phosphinate Bis-Amino Acid and Its Use in the Construction of Amphiphilic Peptides

  摘要：

  A new amphiphilic bis-amino acid has been designed and its convergent, asymmetric synthesis achieved in differentially protected form. A convenient preparation of iodophenylalanine, a generally useful starting material, is disclosed. Sequential palladium-catalyzed couplings of aryl iodides to phosphinate lead directly to the target protected bis-amino acid. Controlled peptide coupling of the new bis-amino acid is also demonstrated.

  DOI：

  10.1021/jo00094a036

文献信息

• Synthesis and binding studies of two new macrocyclic receptors for the stereoselective recognition of dipeptides
  作者：Ana Maria Castilla、M Morgan Conn、Pablo Ballester

  DOI：10.3762/bjoc.6.5

  日期：——

  We present here the design, synthesis, and analysis of a series of receptors for peptide ligands inspired by the hydrogen-bonding pattern of protein β-sheets. The receptors themselves can be regarded as strands 1 and 3 of a three-stranded β-sheet, with cross-linking between the chains through the 4-position of adjacent phenylalanine residues. We also report on the conformational equilibria of these receptors in solution as well as on their tendency to dimerize. ¹H NMR titration experiments are used to quantify the dimerization constants, as well as the association constant values of the 1:1 complexes formed between the receptors and a series of diamides and dipeptides. The receptors show moderate levels of selectivity in the molecular recognition of the hydrogen-bonding pattern present in the diamide series, selecting the α-amino acid-related hydrogen-bonding functionality. Only one of the two cyclic receptors shows modest signs of enantioselectivity and moderate diastereoselectivity in the recognition of the enantiomers and diastereoisomers of the Ala-Ala dipeptide (ΔΔG⁰₁ (DD-DL) = −1.08 kcal/mol and ΔΔG⁰₁ (DD-LD) = −0.89 kcal/mol). Surprisingly, the linear synthetic precursors show higher levels of stereoselectivity than their cyclic counterparts.

  我们在这里介绍了一系列受蛋白质β-折叠中氢键模式启发的肽配体受体的设计、合成和分析。这些受体本身可以被视为一个三股β-折叠中的第一股和第三股，通过相邻苯丙氨酸残基的4位交联链之间的交联。我们还报告了这些受体在溶液中的构象平衡以及它们二聚的倾向。使用1H NMR滴定实验来量化二聚化常数，以及受体和一系列二酰胺和二肽形成的1:1复合物的关联常数值。这些受体在分子识别二酰胺系列中存在的氢键模式方面表现出适度的选择性，选择α-氨基酸相关的氢键功能。仅有两个环状受体中的一个显示出对Ala-Ala二肽的对映体和对映异构体的识别中适度的对映选择性和中等的顺反异构选择性（ΔΔG01（DD-DL）= -1.08 kcal/mol和ΔΔG01（DD-LD）= -0.89 kcal/mol）。令人惊讶的是，线性合成前体显示出比它们的环状对应物更高的立体选择性。
• α-Amino acid Tröger base derivatives, possible conformationally restricted scaffolds?
  作者：Sean P. Bew、Laurent Legentil、Vincent Scholier、Sunil V. Sharma

  DOI：10.1039/b614371g

  日期：——

  The first synthesis of innovative α-amino acid conjugates of Tröger base is reported; their potential application as conformationally restricted scaffolds is proposed and has been investigated using high level ab initio calculations.

  报告首次合成了创新的δ-氨基酸共轭物；提出了它们作为构象受限支架的潜在应用，并利用高水平的ab initio计算对其进行了研究。