Boc-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-OH | 220145-12-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Boc-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-OH
• 英文别名: 3-[[3-[[3-[[3-[[3-[[2,2-Dimethyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-2,2-dimethylpropanoyl]amino]-2,2-dimethylpropanoyl]amino]-2,2-dimethylpropanoyl]amino]-2,2-dimethylpropanoyl]amino]-2,2-dimethylpropanoic acid
• CAS: 220145-12-0
• 化学式: C₃₅H₆₄N₆O₉
• 分子量: 712.928
• InChiKey: BOUBLVQSKRUZPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  50
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  221
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Boc-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-OH 、 CF3COOH*H2N-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-OMe 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以62%的产率得到Boc-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-OMe
  参考文献：
  名称：

  Preparation and Structure ofβ-Peptides Consisting of Geminally Disubstitutedβ2,2- andβ3,3-Amino Acids: A Turn Motif forβ-Peptides

  摘要：

  We report on the synthesis of new and previously described beta-peptides (1-6), consisting of up to twelve beta(2,2-) or beta(3,3)-geminally disubstituted beta-amino acids which do not fit into any of the secondary structural patterns of beta-peptides, hitherto disclosed. The required 2,2- and 3,3-dimethyl derivatives of 3-aminopropanoic acid are readily obtained from 3-methylbut-2-enoic acid and ammonia (Scheme 1) and from Boc-protected methyl 3-aminopropanoate by enolate methylation (Scheme 2). Protected (Boc for solution-, Fmoc for solid-phase syntheses) 1-(aminomethyl)cycloalkanecarboxylic-acid derivatives (with cyclopropane, cyclobutane, cyclopentane, and cyclohexane rings) are obtained from 1-cyanocycloalkanecarboxylates and the corresponding dihaloalkanes (Scheme 3). Fully C-13- and N-15-labeled 3-amino-2,2-dimethylpropanoic-acid derivatives were prepared from the corresponding labeled precursors (see asterixed formula numbers and Scheme 4). Coupling of these amino acids was achieved by methods which we had previously employed for other beta-peptide syntheses ( intermediates 18 - 23). Crystal structures of Boc-protected geminally disubstituted amine acids (16a-d) and of the corresponding tripeptide (23a), as well as NMR and IR spectra of an isotopically labeled beta-hexapeptide (2a*) are presented (Figs. 1-4) and discussed. The tripeptide structure contains a ten-membered H-bonded ring which is proposed to be a turn-forming motif for beta-peptides (Fig. 2).

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2218::aid-hlca2218>3.0.co;2-0
• 作为产物：
  描述：

  3-(叔丁氧基羰基)-2,2-二甲基丙酸甲酯 在 sodium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 67.5h， 生成 Boc-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-β^2,2-HAib-OH
  参考文献：
  名称：

  Preparation and Structure ofβ-Peptides Consisting of Geminally Disubstitutedβ2,2- andβ3,3-Amino Acids: A Turn Motif forβ-Peptides

  摘要：

  We report on the synthesis of new and previously described beta-peptides (1-6), consisting of up to twelve beta(2,2-) or beta(3,3)-geminally disubstituted beta-amino acids which do not fit into any of the secondary structural patterns of beta-peptides, hitherto disclosed. The required 2,2- and 3,3-dimethyl derivatives of 3-aminopropanoic acid are readily obtained from 3-methylbut-2-enoic acid and ammonia (Scheme 1) and from Boc-protected methyl 3-aminopropanoate by enolate methylation (Scheme 2). Protected (Boc for solution-, Fmoc for solid-phase syntheses) 1-(aminomethyl)cycloalkanecarboxylic-acid derivatives (with cyclopropane, cyclobutane, cyclopentane, and cyclohexane rings) are obtained from 1-cyanocycloalkanecarboxylates and the corresponding dihaloalkanes (Scheme 3). Fully C-13- and N-15-labeled 3-amino-2,2-dimethylpropanoic-acid derivatives were prepared from the corresponding labeled precursors (see asterixed formula numbers and Scheme 4). Coupling of these amino acids was achieved by methods which we had previously employed for other beta-peptide syntheses ( intermediates 18 - 23). Crystal structures of Boc-protected geminally disubstituted amine acids (16a-d) and of the corresponding tripeptide (23a), as well as NMR and IR spectra of an isotopically labeled beta-hexapeptide (2a*) are presented (Figs. 1-4) and discussed. The tripeptide structure contains a ten-membered H-bonded ring which is proposed to be a turn-forming motif for beta-peptides (Fig. 2).

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2218::aid-hlca2218>3.0.co;2-0