芴甲氧羰基-缬氨酸-1-13C | 286460-74-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: 芴甲氧羰基-缬氨酸-1-13C
• 英文名称: N-((9-fluorenylmethoxy)carbonyl)-[1-13C]-L-valine
• 英文别名: Fmoc-Val-OH-1-13C；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methyl(113C)butanoic acid
• CAS: 286460-74-0
• 化学式: C₂₀H₂₁NO₄
• 分子量: 340.38
• InChiKey: UGNIYGNGCNXHTR-ZLHLYFPTSA-N

物化性质

• 熔点：
  143-145 °C(lit.)
• 稳定性/保质期：
  避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  芴甲氧羰基-缬氨酸-1-13C 在 盐酸 、 重氧水 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 40.0h， 生成
  参考文献：
  名称：

  A Simple and Economical Method for the Production of ¹³C,¹⁸O-Labeled Fmoc-Amino Acids with High Levels of Enrichment:  Applications to Isotope-Edited IR Studies of Proteins

  摘要：

  Isotope-edited IR of proteins has generated considerable interest. Double labeling with C-13 and O-18 with high levels of isotopic enrichment is required for residue-specific resolution. Current methods for the preparation of doubly labeled amino acids give modest O-18 enrichment, limiting the utility of the approach. We report a simple and economical method for preparing C-13,O-18-doubly labeled N-(9-fluorenylmethoxycarbonyl)-amino acids with high levels of enrichment for residues that do not require acid-labile side-chain protecting groups.

  DOI：

  10.1021/ol701913p
• 作为产物：
  描述：

  L-缬氨酸-1-13C 、 氯甲酸-9-芴基甲酯 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 6.0h， 以89%的产率得到芴甲氧羰基-缬氨酸-1-13C
  参考文献：
  名称：

  A Simple and Economical Method for the Production of ¹³C,¹⁸O-Labeled Fmoc-Amino Acids with High Levels of Enrichment:  Applications to Isotope-Edited IR Studies of Proteins

  摘要：

  Isotope-edited IR of proteins has generated considerable interest. Double labeling with C-13 and O-18 with high levels of isotopic enrichment is required for residue-specific resolution. Current methods for the preparation of doubly labeled amino acids give modest O-18 enrichment, limiting the utility of the approach. We report a simple and economical method for preparing C-13,O-18-doubly labeled N-(9-fluorenylmethoxycarbonyl)-amino acids with high levels of enrichment for residues that do not require acid-labile side-chain protecting groups.

  DOI：

  10.1021/ol701913p

文献信息

• Quantitative Analysis of Multiplex H-Bonds
  作者：Esther S. Brielle、Isaiah T. Arkin

  DOI：10.1021/jacs.0c04357

  日期：2020.8.19

  least one non-canonical H-bond formed by a serine or threonine residue whose hydroxyl side chain H-bonds to an over-coordinated carbonyl oxygen at position i–4, i–3, or i in the sequence. Isotope-edited FTIR spectroscopy, coupled with DFT calculations, enables us to determine the bond enthalpies, pointing to values that are up to 127% higher than that of a single canonical H-bond. We propose that these

  氢键是生物分子结构和相互作用的主要几何决定因素。因此，已经进行了大量分析来研究其详细的能量学。然而，焦点主要集中在包含单个供体和单个受体的 H 键上。在这里，我们测量了三个或更多组之间形成的多重 H 键的普遍性和能量学。我们表明，92% 的跨膜螺旋至少有一个由丝氨酸或苏氨酸残基形成的非规范 H 键，其羟基侧链 H 键与 i-4、i-3 位置的过度配位羰基氧结合，或 i 在序列中。同位素编辑的 FTIR 光谱加上 DFT 计算，使我们能够确定键焓，指向比单个规范 H 键高 127% 的值。
• Cross-Strand Coupling of a β-Hairpin Peptide Stabilized with an Aib-Gly Turn Studied Using Isotope-Edited IR Spectroscopy
  作者：Rong Huang、Vladimir Setnička、Marcus A. Etienne、Joohyun Kim、Jan Kubelka、Robert P. Hammer、Timothy A. Keiderling

  DOI：10.1021/ja0736414

  日期：2007.11.1

  Isotope-edited IR spectroscopy was used to study a series of singly and doubly C-13=O-labeled beta-hairpin peptides stabilized by an Aib-Gly turn sequence. The double-labeled peptides have amide I' IR spectra that show different degrees of vibrational coupling between the C-13-labeled amides due to variations in the local geometry of the peptide structure. The single-labeled peptides provide controls to determine frequencies characteristic of the diagonal force field (FF) contributions at each position for the uncoupled C-13=O modes. Separation of diagonal FF and coupling effects on the spectra are used to explain the cross-strand labeled spectral patterns. DFT calculations based on an idealized model beta-hairpin peptide correctly predict the vibrational coupling patterns. Extending these model results by consideration of frayed ends and the hairpin conformational flexibility yields an alternate interpretation of details of the spectra. Temperature-dependent isotopically labeled IR spectra reveal differences in the thermal stabilities of the individual isotopically labeled sites. This is the first example of using an IR-based isotopic labeling technique to differentiate structural transitions at specific sites along the peptide backbone in model beta-hairpin peptides.
• A Simple and Economical Method for the Production of ¹³C,¹⁸O-Labeled Fmoc-Amino Acids with High Levels of Enrichment:  Applications to Isotope-Edited IR Studies of Proteins
  作者：James Marecek、BenBen Song、Scott Brewer、Jenifer Belyea、R. Brian Dyer、Daniel P. Raleigh

  DOI：10.1021/ol701913p

  日期：2007.11.1

  Isotope-edited IR of proteins has generated considerable interest. Double labeling with C-13 and O-18 with high levels of isotopic enrichment is required for residue-specific resolution. Current methods for the preparation of doubly labeled amino acids give modest O-18 enrichment, limiting the utility of the approach. We report a simple and economical method for preparing C-13,O-18-doubly labeled N-(9-fluorenylmethoxycarbonyl)-amino acids with high levels of enrichment for residues that do not require acid-labile side-chain protecting groups.