O-(1,1-dimethylethyl)-N-(L-leucyl)-D-serine methyl ester | 1337986-88-5

• 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: O-(1,1-dimethylethyl)-N-(L-leucyl)-D-serine methyl ester
• 英文别名: L-Leu-D-Ser(OBu-t)OMe；methyl (2R)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-3-[(2-methylpropan-2-yl)oxy]propanoate
• CAS: 1337986-88-5
• 化学式: C₁₄H₂₈N₂O₄
• 分子量: 288.387
• InChiKey: AIWMVHVUHIUACI-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O-(1,1-dimethylethyl)-N-(L-leucyl)-D-serine methyl ester 在 palladium 10% on activated carbon 、 氢气 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 N-(N-((S)-2-amino-4-cyanobutanoyl)-L-Leucyl)-O-(1,1-dimethylethyl)-D-serine methyl ester
  参考文献：
  名称：

  S-2-Amino-4-cyanobutanoic acid (β-cyanomethyl-l-Ala) as an atom-efficient solubilising synthon for l-glutamine

  摘要：

  Glutamine (Gln) is often a difficult amino acid to incorporate during solution-phase peptide synthesis, owing to poor solubility and unwanted dehydrations as side-reactions. Current approaches to solving these problems are highly atom-inefficient. N(alpha)-Cbz-beta-cyanomethyl-L-Ala is readily accessible by dehydration of Cbz-L-Gln. beta-Cyanomethyl-L-Ala can be incorporated into short peptides easily by conventional methods. The nitrite is stable to the hydrogenolysis conditions used to remove Cbz and to acidic deprotection but is quantitatively hydrated to the gamma-carboxamide of L-Gln with hydrogen peroxide. Thus beta-cyanomethyl-L-Ala may represent a new, soluble, perfectly atom-efficient synthon for L-Gln. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.017
• 作为产物：
  描述：

  (R)-2-amino-3-t-butoxypropionic acid methyl ester 在 palladium 10% on activated carbon 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 O-(1,1-dimethylethyl)-N-(L-leucyl)-D-serine methyl ester
  参考文献：
  名称：

  S-2-Amino-4-cyanobutanoic acid (β-cyanomethyl-l-Ala) as an atom-efficient solubilising synthon for l-glutamine

  摘要：

  Glutamine (Gln) is often a difficult amino acid to incorporate during solution-phase peptide synthesis, owing to poor solubility and unwanted dehydrations as side-reactions. Current approaches to solving these problems are highly atom-inefficient. N(alpha)-Cbz-beta-cyanomethyl-L-Ala is readily accessible by dehydration of Cbz-L-Gln. beta-Cyanomethyl-L-Ala can be incorporated into short peptides easily by conventional methods. The nitrite is stable to the hydrogenolysis conditions used to remove Cbz and to acidic deprotection but is quantitatively hydrated to the gamma-carboxamide of L-Gln with hydrogen peroxide. Thus beta-cyanomethyl-L-Ala may represent a new, soluble, perfectly atom-efficient synthon for L-Gln. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.017

文献信息

• S-2-Amino-4-cyanobutanoic acid (β-cyanomethyl-l-Ala) as an atom-efficient solubilising synthon for l-glutamine
  作者：Anne Beauchard、Elvis A. Twum、Matthew D. Lloyd、Michael D. Threadgill

  DOI：10.1016/j.tetlet.2011.08.017

  日期：2011.10

  Glutamine (Gln) is often a difficult amino acid to incorporate during solution-phase peptide synthesis, owing to poor solubility and unwanted dehydrations as side-reactions. Current approaches to solving these problems are highly atom-inefficient. N(alpha)-Cbz-beta-cyanomethyl-L-Ala is readily accessible by dehydration of Cbz-L-Gln. beta-Cyanomethyl-L-Ala can be incorporated into short peptides easily by conventional methods. The nitrite is stable to the hydrogenolysis conditions used to remove Cbz and to acidic deprotection but is quantitatively hydrated to the gamma-carboxamide of L-Gln with hydrogen peroxide. Thus beta-cyanomethyl-L-Ala may represent a new, soluble, perfectly atom-efficient synthon for L-Gln. (C) 2011 Elsevier Ltd. All rights reserved.