(S)-2-{5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanamido}-3-phenylpropanoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: (S)-2-{5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanamido}-3-phenylpropanoic acid
• 英文别名: N-biotinyl-L-phenylalanine；biotin-Phe-OH；(S)-2-(5-((3AS,4S,6AR)-2-Oxohexahydro-1H-thieno[3,4-D]imidazol-4-YL)pentanamido)-3-phenylpropanoic acid；(2S)-2-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-phenylpropanoic acid
• 化学式: C₁₉H₂₅N₃O₄S
• 分子量: 391.491
• InChiKey: MCMKASCMNHIQTP-JKQORVJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  133
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  D-生物素 在 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 (S)-2-{5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanamido}-3-phenylpropanoic acid
  参考文献：
  名称：

  肽-维生素偶联物的微波辅助形成

  摘要：

  通过使用微波辐射以良好到令人满意的产率合成了具有维生素 B3、H、E 和 D3 的氨基酸和肽缀合物。此外，还引入了一种新型苯并三唑活化的生物素中间体，可作为替代生物素化剂。

  DOI：

  10.1002/ejoc.201200323

文献信息

• PRODUCTION METHOD FOR CHARGED NON-PROTEIN AMINO ACID-CONTAINING PEPTIDE
  申请人：The University of Tokyo

  公开号：EP3031915A1

  公开（公告）日：2016-06-15

  An object of the present invention is to provide a method of producing a peptide containing a charged non-proteinogenic amino acid in a cell-free translation system, and the like. The present invention provides a method of producing a peptide containing a charged non-proteinogenic amino acid. It includes a step of expressing a peptide in a cell-free translation system including (i) at least one tRNA to which a non-proteinogenic amino acid having a protecting-group-introduced charged group has been bound and (ii) a nucleic acid that encodes the peptide and contains at least one codon corresponding to an anticodon of the tRNA; and a step of removing the protecting group of the non-proteinogenic amino acid residue contained in the peptide.

  本发明的目的是提供一种在无细胞翻译系统中生产含有带电非蛋白源氨基酸的多肽的方法等。 本发明提供了一种生产含有带电非蛋白源氨基酸的多肽的方法。它包括在无细胞翻译系统中表达多肽的步骤，无细胞翻译系统包括(i)至少一个tRNA，具有保护基团引入的带电基团的非蛋白源氨基酸与该tRNA结合；(ii)编码多肽的核酸，该核酸含有至少一个与该tRNA的反密码子相对应的密码子；以及去除多肽中含有的非蛋白源氨基酸残基的保护基团的步骤。
• Production method for charged non-protein amino acid-containing peptide
  申请人：The University of Tokyo

  公开号：US10745692B2

  公开（公告）日：2020-08-18

  An object of the present invention is to provide a method of producing a peptide containing a charged non-proteinogenic amino acid in a cell-free translation system, and the like. The present invention provides a method of producing a peptide containing a charged non-proteinogenic amino acid. It includes a step of expressing a peptide in a cell-free translation system including (i) at least one tRNA to which a non-proteinogenic amino acid having a protecting-group-introduced charged group has been bound and (ii) a nucleic acid that encodes the peptide and contains at least one codon corresponding to an anticodon of the tRNA; and a step of removing the protecting group of the non-proteinogenic amino acid residue contained in the peptide.

  本发明的目的是提供一种在无细胞翻译系统中生产含有带电非蛋白源氨基酸的多肽的方法等。 本发明提供了一种生产含有带电非蛋白源氨基酸的多肽的方法。它包括在无细胞翻译系统中表达多肽的步骤，无细胞翻译系统包括(i)至少一个tRNA，具有保护基团引入的带电基团的非蛋白源氨基酸与该tRNA结合；(ii)编码多肽的核酸，该核酸含有至少一个与该tRNA的反密码子相对应的密码子；以及去除多肽中含有的非蛋白源氨基酸残基的保护基团的步骤。
• Ditryptophan Conjugation Triggers Conversion of Biotin Fibers into Soft Spherical Structures
  作者：K. B. Joshi、Sandeep Verma

  DOI：10.1002/anie.200705012

  日期：2008.3.31
• Microwave-Assisted Synthesis of Biotin Conjugates with Quinolone Antibiotics via Amino Acids
  作者：Alan Katritzky、Siva Panda、Roman Naumov、Abdullah Asiri

  DOI：10.1055/s-0033-1340978

  日期：——

  Benzotriazole-activated biotin was utilized as a versatile building block for the efficient and convenient synthesis of novel biotin conjugates with quinolone antibiotics via amino acid linkers under microwave irradiation. The products are obtained in yields of 70-91% with retention of chirality.
• Biotin−Amino Acid Conjugates:  An Approach Toward Self-Assembled Hydrogelation
  作者：Sankarprasad Bhuniya、Sun Min Park、Byeang Hyean Kim

  DOI：10.1021/ol050300r

  日期：2005.4.1

  Amino acid-appended biotin hydrogelators are a new class of low-molecular-weight gelators that display remarkable gelation properties in aqueous media, including buffer solutions with variable pH.