glycine allyl ester | 158840-15-4

• 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: glycine allyl ester
• 英文别名: (S)-allyl 2-(2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)acetate；N-tert-butyloxycarbonyl-L-phenylalanyl-glycine allyl ester；prop-2-enyl 2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]acetate
• CAS: 158840-15-4
• 化学式: C₁₉H₂₆N₂O₅
• 分子量: 362.426
• InChiKey: CRUHAMQQAQYNNX-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  glycine allyl ester 在 四(三苯基膦)钯 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 -2-(2-propenyl)glycine
  参考文献：
  名称：

  Introduction of Allylic Side Chains onto Peptides by Pd(0)-Catalyzed "Ester Enolate Claisen Rearrangement"

  摘要：

  Allylic esters of peptides undergo an ester enolate Claisen rearrangement upon treatment with LDA in the presence of various metal salts (see Table 1). Best results are obtained using zinc chloride. In the presence of a catalytic amount of Pd(0) the rearrangement products are formed in high yields. Addition of Pd(II) has no significant influence on the yield and stereoselectivity of the reaction. In contrast to the rearrangement without Pd(0) the catalyzed reaction probably proceeds; via intermolecular allylic alkylation as is shown in a cross experiment of different allylic esters. The methodology is not limited to dipeptides, but can also be applied to larger peptides as is illustrated in the rearrangement of tripeptide 11. No epimerization of chiral centers is observed under the reaction conditions used.

  DOI：

  10.1021/jo00101a026
• 作为产物：
  描述：

  allyl 2-(4-methylphenylsulfonamido)acetate 、 BOC-L-苯丙氨酸 在 PyBOP 、 N,N-二异丙基乙胺 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以97.5%的产率得到glycine allyl ester
  参考文献：
  名称：

  A Versatile Scaffold for Site-Specific Modification of Cyclic Tetrapeptides

  摘要：

  A novel scaffold that can be used to prepare conformationally homogeneous cyclic tetrapeptides equipped with a beta-amino acid residue is disclosed. It Is shown that regioselective structural modification can be accomplished using thiols and azide nucleophiles, commonly associated with rich downstream chemistry. The method should find application in efforts to constrain privileged tripeptide sequences in rigid molecular scaffolds.

  DOI：

  10.1021/ol301178r

文献信息

• Synthesis of the palmitoylated and prenylated C-terminal lipopeptides of the human R- and N-Ras proteins
  作者：T. Schmittberger、H. Waldmann

  DOI：10.1016/s0968-0896(98)00251-x

  日期：1999.5

  For the study of biological phenomena influenced by the R- and N-Ras proteins, characteristic peptides which embody the correct lipid modifications of their parent proteins (palmitoyl thioesters, geranylgeranyl thioethers, and farnesyl thioethers), as well as analogues thereof, may serve as efficient tools. For the construction of such acid- and base labile peptide conjugates the allyl ester was developed as C-terminal protecting group. Allyl esters are cleaved selectively and in high yields from lipidated peptides by Pd(0)-mediated allyl transfer to accepting N- or C-nucleophiles like morpholine and N,N-dimethylbarbituric acid. This protecting group technique formed the key step in the synthesis of the characteristic S-palmitoylated and S-isoprenylated C-terminus of human R-Ras and human N-Ras proteins, as well as several analogues thereof. Deprotections are so mild that no undesired side reactions of the lipid conjugates are observed. (C) 1999 Elsevier Science Ltd. All rights reserved.
• [EN] CYCLIC AMINO ACID MOLECULES CONTAINING AZIRIDINE AMINO ACIDS AND METHODS OF PREPARING SAME<br/>[FR] MOLÉCULES D'ACIDES AMINÉS CYCLIQUES CONTENANT DES ACIDES AMINÉS D'AZIRIDINE ET LEURS PROCÉDÉS DE PRÉPARATION
  申请人：UNIV TORONTO

  公开号：WO2011150500A1

  公开（公告）日：2011-12-08

  Cyclic amino acid molecules containing aziridine amino acids are provided, as well as methods of preparing same. Linear peptides containing aziridine amino acids and methods of preparing same are also provided.
• A Versatile Scaffold for Site-Specific Modification of Cyclic Tetrapeptides
  作者：Christopher J. White、Andrei K. Yudin

  DOI：10.1021/ol301178r

  日期：2012.6.1

  A novel scaffold that can be used to prepare conformationally homogeneous cyclic tetrapeptides equipped with a beta-amino acid residue is disclosed. It Is shown that regioselective structural modification can be accomplished using thiols and azide nucleophiles, commonly associated with rich downstream chemistry. The method should find application in efforts to constrain privileged tripeptide sequences in rigid molecular scaffolds.
• Introduction of Allylic Side Chains onto Peptides by Pd(0)-Catalyzed "Ester Enolate Claisen Rearrangement"
  作者：Uli Kazmaier

  DOI：10.1021/jo00101a026

  日期：1994.11

  Allylic esters of peptides undergo an ester enolate Claisen rearrangement upon treatment with LDA in the presence of various metal salts (see Table 1). Best results are obtained using zinc chloride. In the presence of a catalytic amount of Pd(0) the rearrangement products are formed in high yields. Addition of Pd(II) has no significant influence on the yield and stereoselectivity of the reaction. In contrast to the rearrangement without Pd(0) the catalyzed reaction probably proceeds; via intermolecular allylic alkylation as is shown in a cross experiment of different allylic esters. The methodology is not limited to dipeptides, but can also be applied to larger peptides as is illustrated in the rearrangement of tripeptide 11. No epimerization of chiral centers is observed under the reaction conditions used.