N-tert-butyloxycarbonyl-(S)-leucylglycine N',N'-dimethylamide | 105141-67-1

• 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-tert-butyloxycarbonyl-(S)-leucylglycine N',N'-dimethylamide
• 英文别名: Boc-L-Leu-Gly-N(CH3)2；tert-butyl N-[(2S)-1-[[2-(dimethylamino)-2-oxoethyl]amino]-4-methyl-1-oxopentan-2-yl]carbamate
• CAS: 105141-67-1
• 化学式: C₁₅H₂₉N₃O₄
• 分子量: 315.413
• InChiKey: GOHQFOLLJXFFTO-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-tert-butyloxycarbonyl-(S)-leucylglycine N',N'-dimethylamide 在 palladium on activated charcoal 盐酸 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 (S)-1-(2-Acetylamino-acetyl)-azetidine-2-carboxylic acid [(S)-1-(dimethylcarbamoylmethyl-carbamoyl)-3-methyl-butyl]-amide
  参考文献：
  名称：

  Conformational Analysis of β-Turn Structure in Tetrapeptides Containing Proline or Proline Analogs

  摘要：

  In order to evaluate the influence of cyclic secondary amino acids on the stability of beta-turn structure, we have prepared Ac-Gly-L-Xxx-L-Leu-Gly-N(CH3)(2) (Xxx = Aze, 4-membered ring: 1, Xxx = Pro, 5-membered ring: 2, Xxx = Pip, 6-membered ring: 3). The NOE cross peaks that support beta-turn structure were observed in 1-3. The NOE cross peak between both terminals of the synthetic peptides, however, was observed only in the NOESY spectra of 2. This result indicates that 5-membered ring side chain in proline plays a very important role in the formation of beta-hairpin structure. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00529-7
• 作为产物：
  描述：

  BOC-L-亮氨酸 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 157.5h， 生成 N-tert-butyloxycarbonyl-(S)-leucylglycine N',N'-dimethylamide
  参考文献：
  名称：

  氨基酸和肽的研究，11.合成四个含有N-末端（S）-5-硫氧杂戊基残基的MIF类似物

  摘要：

  新合成的氨基酸（小号）-5- thioxoproline（（小号）机顶-OH）（1）已被耦合用HCl·H-（小号）-Leu-GlyNRR' 6通过混合酐方法。将得到的三肽酰胺（小号）-Top-（小号）-Leu-GlyNRR' 7是下丘脑因子MIF的新类似物。通过Boc-（S）-Leu-GlyOEt与相应的胺HNRR'的氨解反应，然后用4 M HCl /二恶烷除去Boc基团来合成中间体6。在7的两个合成中，相应的N-羧化三肽酰胺8分离出氯仿，即氯甲酸异丁酯与1反应。减少氯甲酸异丁酯的使用量和活化时间会减少所形成的8的量。

  DOI：

  10.1002/jlac.198719870110

文献信息

• Conformational Analysis of β-Turn Structure in Tetrapeptides Containing Proline or Proline Analogs
  作者：Takashi Hayashi*、Tomohito Asai、Hisanobu Ogoshi*

  DOI：10.1016/s0040-4039(97)00529-7

  日期：1997.4

  In order to evaluate the influence of cyclic secondary amino acids on the stability of beta-turn structure, we have prepared Ac-Gly-L-Xxx-L-Leu-Gly-N(CH3)(2) (Xxx = Aze, 4-membered ring: 1, Xxx = Pro, 5-membered ring: 2, Xxx = Pip, 6-membered ring: 3). The NOE cross peaks that support beta-turn structure were observed in 1-3. The NOE cross peak between both terminals of the synthetic peptides, however, was observed only in the NOESY spectra of 2. This result indicates that 5-membered ring side chain in proline plays a very important role in the formation of beta-hairpin structure. (C) 1997 Elsevier Science Ltd.
• Studies on Amino Acids and Peptides, 11. Synthesis of Four MIF Analogues Containing an N-Terminal (S)-5-Thioxoprolyl Residue
  作者：Torben P. Andersen、Alexander Senning

  DOI：10.1002/jlac.198719870110

  日期：1987.1.31

  The newly synthesized amino acid (S)-5-thioxoproline ((S)-Top-OH) (1) has been coupled with HCl · H-(S)-Leu-GlyNRR′ 6 by the mixed anhydride method. The resulting tripeptide amides (S)-Top-(S)-Leu-GlyNRR′ 7 are new analogues of the hypothalamic factor MIF. The intermediates 6 were synthesized by aminolysis of Boc-(S)-Leu-GlyOEt with the corresponding amine HNRR′ followed by removal of the Boc group

  新合成的氨基酸（小号）-5- thioxoproline（（小号）机顶-OH）（1）已被耦合用HCl·H-（小号）-Leu-GlyNRR' 6通过混合酐方法。将得到的三肽酰胺（小号）-Top-（小号）-Leu-GlyNRR' 7是下丘脑因子MIF的新类似物。通过Boc-（S）-Leu-GlyOEt与相应的胺HNRR'的氨解反应，然后用4 M HCl /二恶烷除去Boc基团来合成中间体6。在7的两个合成中，相应的N-羧化三肽酰胺8分离出氯仿，即氯甲酸异丁酯与1反应。减少氯甲酸异丁酯的使用量和活化时间会减少所形成的8的量。