isobutylmalonic acid monobenzyl ester | 91682-30-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: isobutylmalonic acid monobenzyl ester
• 英文别名: 4-methyl-2-phenylmethoxycarbonylpentanoic acid
• CAS: 91682-30-3
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: QENYEZHZIITSJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  isobutylmalonic acid monobenzyl ester 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 2-[(1S,2R)-1-((S)-2-Amino-3-phenyl-propionylamino)-2-benzyloxy-propylcarbamoyl]-4-methyl-pentanoic acid benzyl ester; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Partially Modified Retro-Inverso Pseudopeptides as Non-natural Ligands for the Human Class I Histocompatibility Molecule HLA-A2

  摘要：

  Syntheses of a series of partially modified retro-inverso analogues of the antigenic peptide M58-66 derived from the influenza virus matrix protein are reported. The retro-inverso modification Psi(NH-CO) was obtained by replacement of two successive amino acid residues with a 2-substituted malonate derivative and gem-diaminoalkyl residue. The resulting compounds 1-8 were tested for their binding to the human histocompatibility class I molecule HLA-A2 in an assembly assay using lysates of peptide transporter-deficient cells T2. Specific peptide-dependent HLA-A2 assembly was revealed by an enzyme-linked immunosorbent assay. Significant HLA-A2 assembly was detected in the presence of analogues [gGly(58)-(S)mLeu(59)]-M58-66 (1a), [gGly(61)-(R,S)mPhe(62)]M58-66 (4), [gVal(63)-(R,S)mPhe(64)]M58-66 (6), and [gPhe(64)-(R,S)mAla(65)]M58-66 (7). The introduction of the retro-inverso modification between P2-P3, P3-P4, P5-P6, and P8-P9 (compounds 2, 3, 5, and 8, respectively) however led to a dramatic reduction in peptide binding to HLA-A2. Interestingly, compound 1a which contains modification between P1-P2 was found to be the most potent analogue, being able to retain the original HLA-A2 binding profile of the parent peptide M58-66. Taken together, these results and recent binding data obtained in the context of murine MHC class I molecule H-2K(d) suggest that the incorporation of peptide bond surrogates in MHC class I-restricted epitopes is a useful approach to design molecules having both increased stability and high MHC-binding capacity. Depending on their agonist or antagonist effects at the T-cell receptor, such non-natural MHC ligands are likely to find many applications in the development of peptide-based vaccines or as potential therapeutic agents in the treatment of allergies and autoimmune diseases.

  DOI：

  10.1021/jm9509511
• 作为产物：
  描述：

  dibenzyl 2-isobutylmalonate 在 氢氧化钾 作用下， 以 ice-water 、 苯甲醇 为溶剂， 生成 isobutylmalonic acid monobenzyl ester
  参考文献：
  名称：

  6-Acyl derivatives of aminopenicillanic acid

  摘要：

  以下化合物的化学式为##STR1## 其中R为氢，低烷酰氧甲基，低烷基，茚环基或由式子##STR2##所代表的基团，其中X可以是氢，卤素，羟基，低烷基，低烷氧基或低烷氧基-低烷基基团，其药学上可接受的盐和水合物。这些化合物可用作抗生素。

  公开号：

  US04005073A1

文献信息

• US4005073A
  申请人：——

  公开号：US4005073A

  公开（公告）日：1977-01-25
• Partially Modified Retro-Inverso Pseudopeptides as Non-natural Ligands for the Human Class I Histocompatibility Molecule HLA-A2
  作者：Gilles Guichard、Francine Connan、Roland Graff、Marina Ostankovitch、Sylviane Muller、Jean-Gérard Guillet、Jeannine Choppin、Jean-Paul Briand

  DOI：10.1021/jm9509511

  日期：1996.1.1

  Syntheses of a series of partially modified retro-inverso analogues of the antigenic peptide M58-66 derived from the influenza virus matrix protein are reported. The retro-inverso modification Psi(NH-CO) was obtained by replacement of two successive amino acid residues with a 2-substituted malonate derivative and gem-diaminoalkyl residue. The resulting compounds 1-8 were tested for their binding to the human histocompatibility class I molecule HLA-A2 in an assembly assay using lysates of peptide transporter-deficient cells T2. Specific peptide-dependent HLA-A2 assembly was revealed by an enzyme-linked immunosorbent assay. Significant HLA-A2 assembly was detected in the presence of analogues [gGly(58)-(S)mLeu(59)]-M58-66 (1a), [gGly(61)-(R,S)mPhe(62)]M58-66 (4), [gVal(63)-(R,S)mPhe(64)]M58-66 (6), and [gPhe(64)-(R,S)mAla(65)]M58-66 (7). The introduction of the retro-inverso modification between P2-P3, P3-P4, P5-P6, and P8-P9 (compounds 2, 3, 5, and 8, respectively) however led to a dramatic reduction in peptide binding to HLA-A2. Interestingly, compound 1a which contains modification between P1-P2 was found to be the most potent analogue, being able to retain the original HLA-A2 binding profile of the parent peptide M58-66. Taken together, these results and recent binding data obtained in the context of murine MHC class I molecule H-2K(d) suggest that the incorporation of peptide bond surrogates in MHC class I-restricted epitopes is a useful approach to design molecules having both increased stability and high MHC-binding capacity. Depending on their agonist or antagonist effects at the T-cell receptor, such non-natural MHC ligands are likely to find many applications in the development of peptide-based vaccines or as potential therapeutic agents in the treatment of allergies and autoimmune diseases.
• 6-Acyl derivatives of aminopenicillanic acid
  申请人：Hoffmann-La Roche Inc.

  公开号：US04005073A1

  公开（公告）日：1977-01-25

  Compounds represented by the following formula ##STR1## wherein R is hydrogen, lower alkanoyloxymethyl, lower alkyl, indanyl or a radical represented by the formula ##STR2## wherein X may be hydrogen, halogen, hydroxy, lower alkyl, lower alkoxy or a lower alkoxy-lower alkyl group, Pharmaceutically acceptable salts and hydrates thereof. These compounds are useful as antibiotics.

  以下化合物的化学式为##STR1## 其中R为氢，低烷酰氧甲基，低烷基，茚环基或由式子##STR2##所代表的基团，其中X可以是氢，卤素，羟基，低烷基，低烷氧基或低烷氧基-低烷基基团，其药学上可接受的盐和水合物。这些化合物可用作抗生素。