methyl (2S)-2-[[(2S)-2-acetamido-3-(5-amino-2-hydroxyphenyl)propanoyl]amino]propanoate | 1027892-43-8

• 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: methyl (2S)-2-[[(2S)-2-acetamido-3-(5-amino-2-hydroxyphenyl)propanoyl]amino]propanoate
• CAS: 1027892-43-8
• 化学式: C₁₅H₂₁N₃O₅
• 分子量: 323.349
• InChiKey: VYBXRPBRVWYIFQ-UFBFGSQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[(2S)-2-acetamido-3-(5-amino-2-hydroxyphenyl)propanoyl]amino]propanoate 在 溶剂黄146 、 亚硝酸异戊酯 作用下， 生成 Ac-L-o-Dip-Ala-OMe
  参考文献：
  名称：

  Design of New Photoactivatable Amino Acids: Stereoselective Synthesis of N-Protected Phenylalanine Derivatives as Precursors of p-Diazocyclohexadienone-Containing Peptides

  摘要：

  4-Diazocyclohexa-2,5-dienone-based amino acids m-Dip and o-Dip were designed for building up photoactivatable peptides. Their stable precursors L-3-[3-(benzyloxy)-6-nitrophenyl]alanine (L-m-Nip(Bn)) and L-3-[2-(benzyloxy)-5-nitrophenyl]alanine (L-o-Nip(Bn)) were synthesized by stereoselective alkylation of the corresponding benzyloxynitrobenzyl iodides by a chiral glycine equivalent. Alkylation was carried out using either butyllithium in dry organic solvents or a phase transfer procedure. Alkylation, hydrolysis of the adduct, and protection as Boc and Fmoc derivatives were achieved in 57-73% overall yields and led to 97-99% optically pure material. Boc or Fmoc-m/o-Nip(Bn) was inserted in model dipeptides Ac-mlo-Nip(Bn)-Ala-OMe or tripeptides Ala-Lm-Nip-(Bn)-Lys and Ala-L-o-Nip(Bn)-Arg, respectively, by homogeneous solution procedure and by solid-phase peptide synthesis. Deprotection and diazotization of the resulting p-hydroxyanilines gave the corresponding photoactivatable 4-diazocyclohexa-2,5-dienones containing peptides in quantitative yields. Such photoprobes are stable for several hours in the dark but are rapidly photolyzed at 350 nm or at 295 nm by a tryptophan-mediated energy transfer activation process.

  DOI：

  10.1021/jo00108a023
• 作为产物：
  描述：

  2-羟基-5-硝基苄醇 在 palladium on activated charcoal N-甲基吗啉 、 lithium hydroxide 、 sodium hydroxide 、 四丁基溴化铵 、 氢气 、 四丁基硫酸氢铵 、 sodium hydride 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 sodium iodide 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， -10.0~40.0 ℃ 、399.97 Pa 条件下， 反应 10.5h， 生成 methyl (2S)-2-[[(2S)-2-acetamido-3-(5-amino-2-hydroxyphenyl)propanoyl]amino]propanoate
  参考文献：
  名称：

  Design of New Photoactivatable Amino Acids: Stereoselective Synthesis of N-Protected Phenylalanine Derivatives as Precursors of p-Diazocyclohexadienone-Containing Peptides

  摘要：

  4-Diazocyclohexa-2,5-dienone-based amino acids m-Dip and o-Dip were designed for building up photoactivatable peptides. Their stable precursors L-3-[3-(benzyloxy)-6-nitrophenyl]alanine (L-m-Nip(Bn)) and L-3-[2-(benzyloxy)-5-nitrophenyl]alanine (L-o-Nip(Bn)) were synthesized by stereoselective alkylation of the corresponding benzyloxynitrobenzyl iodides by a chiral glycine equivalent. Alkylation was carried out using either butyllithium in dry organic solvents or a phase transfer procedure. Alkylation, hydrolysis of the adduct, and protection as Boc and Fmoc derivatives were achieved in 57-73% overall yields and led to 97-99% optically pure material. Boc or Fmoc-m/o-Nip(Bn) was inserted in model dipeptides Ac-mlo-Nip(Bn)-Ala-OMe or tripeptides Ala-Lm-Nip-(Bn)-Lys and Ala-L-o-Nip(Bn)-Arg, respectively, by homogeneous solution procedure and by solid-phase peptide synthesis. Deprotection and diazotization of the resulting p-hydroxyanilines gave the corresponding photoactivatable 4-diazocyclohexa-2,5-dienones containing peptides in quantitative yields. Such photoprobes are stable for several hours in the dark but are rapidly photolyzed at 350 nm or at 295 nm by a tryptophan-mediated energy transfer activation process.

  DOI：

  10.1021/jo00108a023

文献信息

• Design of New Photoactivatable Amino Acids: Stereoselective Synthesis of N-Protected Phenylalanine Derivatives as Precursors of p-Diazocyclohexadienone-Containing Peptides
  作者：C. Dugave

  DOI：10.1021/jo00108a023

  日期：1995.2

  4-Diazocyclohexa-2,5-dienone-based amino acids m-Dip and o-Dip were designed for building up photoactivatable peptides. Their stable precursors L-3-[3-(benzyloxy)-6-nitrophenyl]alanine (L-m-Nip(Bn)) and L-3-[2-(benzyloxy)-5-nitrophenyl]alanine (L-o-Nip(Bn)) were synthesized by stereoselective alkylation of the corresponding benzyloxynitrobenzyl iodides by a chiral glycine equivalent. Alkylation was carried out using either butyllithium in dry organic solvents or a phase transfer procedure. Alkylation, hydrolysis of the adduct, and protection as Boc and Fmoc derivatives were achieved in 57-73% overall yields and led to 97-99% optically pure material. Boc or Fmoc-m/o-Nip(Bn) was inserted in model dipeptides Ac-mlo-Nip(Bn)-Ala-OMe or tripeptides Ala-Lm-Nip-(Bn)-Lys and Ala-L-o-Nip(Bn)-Arg, respectively, by homogeneous solution procedure and by solid-phase peptide synthesis. Deprotection and diazotization of the resulting p-hydroxyanilines gave the corresponding photoactivatable 4-diazocyclohexa-2,5-dienones containing peptides in quantitative yields. Such photoprobes are stable for several hours in the dark but are rapidly photolyzed at 350 nm or at 295 nm by a tryptophan-mediated energy transfer activation process.