(4R,5S)-3-((S)-2-{[(4R,5S)-3-((S)-2-{[(4R,5S)-3-((S)-2-tert-Butoxycarbonylamino-propionyl)-5-methyl-2-oxo-oxazolidine-4-carbonyl]-amino}-propionyl)-5-methyl-2-oxo-oxazolidine-4-carbonyl]-amino}-propionyl)-5-methyl-2-oxo-oxazolidine-4-carboxylic acid | 879505-87-0

• 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: (4R,5S)-3-((S)-2-{[(4R,5S)-3-((S)-2-{[(4R,5S)-3-((S)-2-tert-Butoxycarbonylamino-propionyl)-5-methyl-2-oxo-oxazolidine-4-carbonyl]-amino}-propionyl)-5-methyl-2-oxo-oxazolidine-4-carbonyl]-amino}-propionyl)-5-methyl-2-oxo-oxazolidine-4-carboxylic acid
• CAS: 879505-87-0
• 化学式: C₂₉H₄₀N₆O₁₅
• 分子量: 712.668
• InChiKey: MIYNPZCQXCUHJG-WJELOMALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  50.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  273.66
• 氢给体数：
  4.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  (4R,5S)-3-((S)-2-{[(4R,5S)-3-((S)-2-{[(4R,5S)-3-((S)-2-tert-Butoxycarbonylamino-propionyl)-5-methyl-2-oxo-oxazolidine-4-carbonyl]-amino}-propionyl)-5-methyl-2-oxo-oxazolidine-4-carbonyl]-amino}-propionyl)-5-methyl-2-oxo-oxazolidine-4-carboxylic acid 在 palladium on activated charcoal 氢气 、 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.67h， 生成 Boc-(L-Ala-D-Oxd)4-OH
  参考文献：
  名称：

  Oxazolidin-2-one-Containing Pseudopeptides That Fold into β-Bend Ribbon Spirals

  摘要：

  Three sets of oligomers containing the 4-carboxy-5-methyloxazolidin-2-one (Oxd) moiety have been synthesized with the aim of checking whether these molecules are able to fold in ordered structures: A set [Boc-(L-Ala-L-Oxd),-OR], B set [BOC-(L-Ala-D-Oxd)(n)-OR], and C set [Boc-(Aib-L-Oxd)(n)-OR] preferential conformations have been analyzed with IR absorption, NMR, and CID. We have noticed that in these oligomers three stabilizing effects are active: (i) the rigid Oxd -CO-N(CH <)-CO- moiety, which always tend to assume a trans conformation; (ii) the formation of Oxd C=(OH)-H-...-C-alpha intramolecolar H-bonds; (iii) the alternate formation of 1 - 4 intramolecular C=(OH)-H-...-N H-bonds. Through the analysis of the experimental data, we could demonstrate that only the oligomers of the B set are able to meet all three requirements listed above. By a deeper insight into the CD spectra, we gathered that the secondary structure adopted by the B set oligomers is a beta-bend ribbon spiral, which is a subtype of the 3(10)-helix.

  DOI：

  10.1021/ja056762h
• 作为产物：
  描述：

  Boc-L-Ala-D-Oxd-OBn 在 palladium on activated charcoal 氢气 、 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 7.34h， 生成 (4R,5S)-3-((S)-2-{[(4R,5S)-3-((S)-2-{[(4R,5S)-3-((S)-2-tert-Butoxycarbonylamino-propionyl)-5-methyl-2-oxo-oxazolidine-4-carbonyl]-amino}-propionyl)-5-methyl-2-oxo-oxazolidine-4-carbonyl]-amino}-propionyl)-5-methyl-2-oxo-oxazolidine-4-carboxylic acid
  参考文献：
  名称：

  Oxazolidin-2-one-Containing Pseudopeptides That Fold into β-Bend Ribbon Spirals

  摘要：

  Three sets of oligomers containing the 4-carboxy-5-methyloxazolidin-2-one (Oxd) moiety have been synthesized with the aim of checking whether these molecules are able to fold in ordered structures: A set [Boc-(L-Ala-L-Oxd),-OR], B set [BOC-(L-Ala-D-Oxd)(n)-OR], and C set [Boc-(Aib-L-Oxd)(n)-OR] preferential conformations have been analyzed with IR absorption, NMR, and CID. We have noticed that in these oligomers three stabilizing effects are active: (i) the rigid Oxd -CO-N(CH <)-CO- moiety, which always tend to assume a trans conformation; (ii) the formation of Oxd C=(OH)-H-...-C-alpha intramolecolar H-bonds; (iii) the alternate formation of 1 - 4 intramolecular C=(OH)-H-...-N H-bonds. Through the analysis of the experimental data, we could demonstrate that only the oligomers of the B set are able to meet all three requirements listed above. By a deeper insight into the CD spectra, we gathered that the secondary structure adopted by the B set oligomers is a beta-bend ribbon spiral, which is a subtype of the 3(10)-helix.

  DOI：

  10.1021/ja056762h

文献信息

• Pseudopeptide Foldamers designed for photoinduced intramolecular electron transfer
  作者：Lorenzo Milli、Enrico Marchi、Nicola Castellucci、Maria Teresa Indelli、Margherita Venturi、Paola Ceroni、Claudia Tomasini

  DOI：10.1039/c4ra13978j

  日期：——

  Hybrid foldamers equipped with a donor and an acceptor unit exhibit unexpected conformations affecting the photoinduced electron transfer ability. The donor quenching efficiency depends both on the nature and on the secondary structure of the linker.

  具有供体和受体单元的混合折叠体表现出意想不到的构象，影响了光诱导电子转移能力。供体猝灭效率取决于连接物的性质和次级结构。
• The Design and Synthesis of Dansyl-Containing Cyclic Pseudopeptides
  作者：Gaetano Angelici、Roger Tresanchez Carrera、Gianlugi Luppi、Claudia Tomasini

  DOI：10.1002/ejoc.200800248

  日期：2008.7

  Six cyclic pseudopeptides with the general formula cyclo-(L-AA-D-Oxd)n [where AA is an α-amino acid, D-Oxd is trans-(4R,5S)-4-carboxy-5-methyloxazolidin-2-one and n = 3, 4] have been designed and efficiently synthesized in the liquid phase in good overall yields. The crucial step is the macrocyclization, which always occurs in satisfactory yields regardless of the cycle dimension and the nature of

  六种环状假肽，通式为 cyclo-(L-AA-D-Oxd)n [其中 AA 是 α-氨基酸，D-Oxd 是反式-(4R,5S)-4-carboxy-5-methyloxazolidin-2 -one 和 n = 3, 4] 已被设计并在液相中以良好的总产率有效合成。关键的步骤是大环化，无论循环维度和侧链中各种官能团的性质如何，它总是以令人满意的产率发生。此外，丹磺酰基（dansyl = 5-二甲氨基-1-萘基磺酰基）单元被引入侧链，目的是制备易于在生物环境中定位的标记环肽。(© Wiley-VCH Verlag GmbH & Co. KGAA, 69451 Weinheim, Germany, 2008)