N-[4-[[(1,1-Dimethylethoxy)carbonyl]amino]butyl]glycine | 174799-98-5

• 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: N-[4-[[(1,1-Dimethylethoxy)carbonyl]amino]butyl]glycine
• 英文别名: 2-[4-[(2-methylpropan-2-yl)oxycarbonylamino]butylamino]acetic acid
• CAS: 174799-98-5
• 化学式: C₁₁H₂₂N₂O₄
• 分子量: 246.307
• InChiKey: OMZISSUTGXJTJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 N-[4-[[(1,1-Dimethylethoxy)carbonyl]amino]butyl]glycine 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以79.4%的产率得到Fmoc-N-(4-Boc-氨丁基)-Gly-OH
  参考文献：
  名称：

  Building Units for N-Backbone Cyclic Peptides. 3. Synthesis of Protected N^α-(ω-Aminoalkyl)amino Acids and N^α-(ω-Carboxyalkyl)amino Acids

  摘要：

  An improved synthesis of a family of amino acids that contain omega-aminoalkyl groups and of a new family containing omega-carboxyalkyl groups linked to the alpha-amine is described. The synthesis was performed by alkylation of suitably monoprotected alkylenediamines and protected omega-amino acids with triflates of alpha-hydroxy acid esters. The reaction proceeded with inversion of configuration yielding optically pure products. The N-alpha-(omega-aminoalkyl)amino acids and N-alpha-(omega-carboxyalkyl)amino acids were orthogonally protected to allow their incorporation into peptides by solid-phase peptide synthesis (SPPS) methodology.

  DOI：

  10.1021/jo961580e
• 作为产物：
  描述：

  tert-butyl 4-(benzylamino)butylcarbamate 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 7.5h， 生成 N-[4-[[(1,1-Dimethylethoxy)carbonyl]amino]butyl]glycine
  参考文献：
  名称：

  Building Units for N-Backbone Cyclic Peptides. 3. Synthesis of Protected N^α-(ω-Aminoalkyl)amino Acids and N^α-(ω-Carboxyalkyl)amino Acids

  摘要：

  An improved synthesis of a family of amino acids that contain omega-aminoalkyl groups and of a new family containing omega-carboxyalkyl groups linked to the alpha-amine is described. The synthesis was performed by alkylation of suitably monoprotected alkylenediamines and protected omega-amino acids with triflates of alpha-hydroxy acid esters. The reaction proceeded with inversion of configuration yielding optically pure products. The N-alpha-(omega-aminoalkyl)amino acids and N-alpha-(omega-carboxyalkyl)amino acids were orthogonally protected to allow their incorporation into peptides by solid-phase peptide synthesis (SPPS) methodology.

  DOI：

  10.1021/jo961580e

文献信息

• Peptide splicing in a double‐sequence analogue of trypsin inhibitor SFTI‐1 substituted in the P ₁ positions by peptoid monomers
  作者：Natalia Karna、Dawid Dębowski、Anna Łęgowska、Remigiusz Bąchor、Zbigniew Szewczuk、Krzysztof Rolka

  DOI：10.1002/bip.22659

  日期：2015.5

  described a process of trypsin‐assisted peptide splicing of analogs of trypsin inhibitor SFTI‐1, that seems to be very similar to proteasome‐catalyzed peptide splicing. Here, we show, for the first time, that a peptide–peptoid hybrid (peptomer) can also be spliced by trypsin. Incubation of a double sequence SFTI‐1 analog, containing two peptoid monomers, with equimolar amount of trypsin leads to formation

  最近，我们描述了胰蛋白酶抑制剂SFTI-1类似物的胰蛋白酶辅助肽剪接的过程，这似乎与蛋白酶体催化的肽剪接非常相似。在这里，我们首次展示了胰蛋白酶也可以剪接肽-类肽杂化物（肽）。含有两个类肽单体和等摩尔量的胰蛋白酶的双序列SFTI-1类似物的孵育导致形成单环肽作为主要产物。我们证明了类肽单体形成的肽键不仅被胰蛋白酶消化，而且还参与了酶辅助的剪接过程。©2015 Wiley Periodicals，Inc.生物聚合物（Pept Sci）104：206–212，2015年。
• BRIDGED LIPOGLYCOPEPTIDES THAT POTENTIATE THE ACTIVITY OF BETA-LACTAM ANTIBACTERIALS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP2544702A1

  公开（公告）日：2013-01-16
• Building Units for N-Backbone Cyclic Peptides. 3. Synthesis of Protected <i>N</i>^α-(ω-Aminoalkyl)amino Acids and <i>N</i>^α-(ω-Carboxyalkyl)amino Acids
  作者：Dan Muller、Irena Zeltser、Gal Bitan、Chaim Gilon

  DOI：10.1021/jo961580e

  日期：1997.1.1

  An improved synthesis of a family of amino acids that contain omega-aminoalkyl groups and of a new family containing omega-carboxyalkyl groups linked to the alpha-amine is described. The synthesis was performed by alkylation of suitably monoprotected alkylenediamines and protected omega-amino acids with triflates of alpha-hydroxy acid esters. The reaction proceeded with inversion of configuration yielding optically pure products. The N-alpha-(omega-aminoalkyl)amino acids and N-alpha-(omega-carboxyalkyl)amino acids were orthogonally protected to allow their incorporation into peptides by solid-phase peptide synthesis (SPPS) methodology.
• Antimicrobial Activity of Peptidomimetics against Multidrug-Resistant Escherichia coli: A Comparative Study of Different Backbones
  作者：Rasmus D. Jahnsen、Niels Frimodt-Møller、Henrik Franzyk

  DOI：10.1021/jm300820a

  日期：2012.8.23

  Novel remedies in the battle against multidrug-resistant bacterial strains are urgently needed, and one obvious approach involves antimicrobial peptides and mimics hereof. The impact of alpha- and beta-peptoid as well as beta(3)-amino acid modifications on the activity profile against beta-lactamase-producing Escherichia coli was assessed by testing an array comprising different types of cationic peptidomimetics obtained by a general monomer-based solid-phase synthesis protocol. Most of the peptidomimetics possessed high to moderate activity toward multidrug-resistant E. coli as opposed to the corresponding inactive peptides. Nevertheless, differences in hemolytic activities indicate that a careful choice of backbone design constitutes a significant parameter in the search for effective cationic antimicrobial peptidomimetics targeting specific bacteria.