methyl 2-methyl-2-(2-nitrophenylsulfonamido)propanoate | 1401065-85-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-methyl-2-(2-nitrophenylsulfonamido)propanoate
• 英文别名: Methyl 2-methyl-2-[(2-nitrophenyl)sulfonylamino]propanoate
• CAS: 1401065-85-7
• 化学式: C₁₁H₁₄N₂O₆S
• 分子量: 302.308
• InChiKey: IINHQRGBGUHQEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-methyl-2-(2-nitrophenylsulfonamido)propanoate 在 甲酸铵 、 锌 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以97%的产率得到methyl 2-methyl-2-(2-aminophenylsulfonamido)propanoate
  参考文献：
  名称：

  An unusual conformational similarity of two peptide folds featuring sulfonamide and carboxamide on the backbone

  摘要：

  已证明在多肽折叠的核心位置具有羧酰胺和磺酰胺的双折多肽具有几乎相似的构象特征，尽管众所周知，羧酰胺和磺酰胺在氢键结合和几何形态上有明显的差异。

  DOI：

  10.1039/c2cc34533a
• 作为产物：
  描述：

  2-amino-2-methylpropionic acid methyl ester 、 邻硝基苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 methyl 2-methyl-2-(2-nitrophenylsulfonamido)propanoate
  参考文献：
  名称：

  Reversal of H-bonding direction by N-sulfonation in a synthetic reverse-turn peptide motif

  摘要：

  这手稿描述了一种有趣的例子，即在合成反转肽的N-末端引入磺胺链后，氢键反转。

  DOI：

  10.1039/c4ob02438a

文献信息

• Orthanilic acid-promoted reverse turn formation in peptides
  作者：Sangram S. Kale、Gowri Priya、Amol S. Kotmale、Rupesh L. Gawade、Vedavati G. Puranik、P. R. Rajamohanan、Gangadhar J. Sanjayan

  DOI：10.1039/c3cc40522b

  日期：——

  Orthanilic acid (2-aminobenzenesulfonic acid, (S)Ant), an aromatic beta-amino acid, has been shown to be highly useful in inducing a folded conformation in peptides. When incorporated into peptide sequences (Xaa-(S)Ant-Yaa), this rigid aromatic beta-amino acid strongly imparts a reverse-turn conformation to the peptide backbone, featuring robust 11-membered-ring hydrogen-bonding.

  邻苯二甲酸（2-氨基苯磺酸，（S）Ant），一种芳香族β-氨基酸，已被证明在诱导肽中的折叠构象方面非常有用。当掺入肽序列（Xaa-（S）Ant-Yaa）中时，该刚性芳族β-氨基酸强烈赋予肽主链反向构象，具有牢固的11元环氢键。
• Conformational modulation of peptide secondary structures using β-aminobenzenesulfonic acid
  作者：Sangram S. Kale、Shrikant M. Kunjir、Rupesh L. Gawade、Vedavati G. Puranik、P. R. Rajamohanan、Gangadhar J. Sanjayan

  DOI：10.1039/c3cc48850k

  日期：——

  This communication describes the influence of beta-aminobenzenesulfonic acid ((S)Ant) on the conformational preferences of hetero foldamers. The designed (Aib-(S)Ant-Aib)n and (Aib-(S)Ant-Pro)n oligomers display a well-defined folded conformation featuring intramolecular mixed hydrogen bonding (7/11) and intra-residual (6/5) H-bonding interactions, respectively.

  此通信描述了β-氨基苯磺酸（（S）Ant）对杂合折叠剂构象偏好的影响。设计的（Aib-（S）Ant-Aib）n和（Aib-（S）Ant-Pro）n低聚物显示出明确定义的折叠构象，具有分子内混合氢键（7/11）和残基内（6 / 5）分别为氢键相互作用。
• Carboxamide versus Sulfonamide in Peptide Backbone Folding: A Case Study with a Hetero Foldamer
  作者：Veera V. E. Ramesh、Sangram S. Kale、Amol S. Kotmale、Rupesh L. Gawade、Vedavati G. Puranik、P. R. Rajamohanan、Gangadhar J. Sanjayan

  DOI：10.1021/ol4002762

  日期：2013.4.5

  Strikingly dissimilar hydrogen-bonding patterns have been observed for two sets of closely similar hetero foldamers containing carboxamide and sulfonamides at regular intervals. Although both foldamers maintain conformational ordering, the hydrogen-bonding pattern and backbone helical handedness differ diametrically.
• PEPTIDE SYNTHESIS METHOD FOR SUPPRESSING DEFECT CAUSED BY DIKETOPIPERAZINE FORMATION
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US20230391818A1

  公开（公告）日：2023-12-07

  Solid-phase synthesis of a peptide has a problem that a desired elongation reaction is prevented from proceeding by diketopiperazine and a 6-membered diamine skeleton compound formed when a protective group at the N-terminal is removed. The present inventors have found that when in production of a peptide by a solid-phase method, a peptide in which an amino group at the N-terminal is protected with a protective group having an Fmoc skeleton is treated in a specific solvent with a base having a pKa of 23 or more in acetonitrile as a conjugate acid, and a peptide chain is then elongated, it is possible to solve the problem described above.