L-difluoromethionine | 126027-81-4

• 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: L-difluoromethionine
• 英文别名: difluoromethionine；(2S)-2-amino-4-(difluoromethylsulfanyl)butanoic acid
• CAS: 126027-81-4
• 化学式: C₅H₉F₂NO₂S
• 分子量: 185.195
• InChiKey: YHBNXKYHZMAFED-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  88.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  L-difluoromethionine 在 1-羟基苯并三唑 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成
  参考文献：
  名称：

  Syntheses of and chemotactic responses elicited by fMet-Leu-Phe analogs containing difluoro- and trifluoromethionine

  摘要：

  N-Formylmethionylleucylphenylalanine tripeptides containing either L-difluoro-or L-trifluoromethionine as replacements for methionine were synthesized by solution methods. The fluorinated peptides were found to have potent chemoattractant activities on human neutrophils. Ab initio calculations were utilized to further understand the changes in electronic properties of the methionine side chain upon fluorination. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10134-2
• 作为产物：
  描述：

  difluoromethylhomocysteine 在 pig liver acylase 作用下， 以24%的产率得到L-difluoromethionine
  参考文献：
  名称：

  氟化蛋氨酸的简便合成

  摘要：

  由N-乙酰同型半胱氨酸硫代内酯（3）有效地制备了L-二氟和三氟甲基同型半胱氨酸（6）和（7），由保护的甲硫氨酸亚砜（1）合成了保护的单氟甲基同型半胱氨酸（2）。

  DOI：

  10.1039/c39890000761

文献信息

• Fluorine-containing amino acids and their derivatives. 9. Synthesis and biological activities of difluoromethylhomocysteine
  作者：Tadahiko Tsushima、Shoichi Ishihara、Yusuke Fujita

  DOI：10.1016/s0040-4039(00)89013-9

  日期：——

  A new fluorine-containing amino acid, difluoromethylhomocystein, was prepared in a chiral form. Some of its biological activities are described.

  以手性形式制备了一种新的含氟氨基酸二氟甲基同型半胱氨酸。描述了其一些生物活性。
• Reduction Potential Tuning of the Blue Copper Center in <i>Pseudomonas </i><i>aeruginosa</i> Azurin by the Axial Methionine as Probed by Unnatural Amino Acids
  作者：Dewain K. Garner、Mark D. Vaughan、Hee Jung Hwang、Masha G. Savelieff、Steven M. Berry、John F. Honek、Yi Lu

  DOI：10.1021/ja062732i

  日期：2006.12.1

  The conserved axial ligand methionine 121 from Pseudomonas aeruginosa azurin (Az) has been replaced by isostructural unnatural amino acid analogues, oxomethionine (OxM), difluoromethionine (DFM), trifluoromethionine (TFM), selenomethionine (SeM), and norleucine (NIe) using expressed protein ligation. The replacements resulted in < 6 nm shifts in the S(Cys)-Cu charge transfer (CT) band in the electronic absorption spectra and < 8 gauss changes in the copper hyperfine coupling constants (A(parallel to)) in the X-band electron paramagnetic resonance spectra, suggesting that isostructural replacement of Met resulted in minimal structural perturbation of the copper center. The slight blue shifts of the CT band follow the trend of stronger electronegativity of the ligands. This trend is supported by F-19 NMR studies of the fluorinated methionine analogues. However, the order of A(parallel to) differs, suggesting additional factors influencing A(parallel to). In contrast to the small changes in the UV-vis and EPR spectra, a large variation of > 227 mV in reduction potential was observed for the series of variants reported here. Additionally, a linear correlation was established between the reduction potentials and hydrophobicity of the variants. Extension of this analysis to other type 1 copper-containing proteins reveals a linear correlation between change in hydrophobicity and change in reduction potential, independent of the protein scaffold, experimental conditions, measurement techniques, and steric modifications. This analysis has also revealed for the first time high and low potential states for type 1 centers, and the difference may be attributable to destabilization of the protein fold by disruption of hydrophobic or hydrogen bonding interactions that stabilize the type 1 center.
• HOUSTON, MICHAEL E. (JR);HONEK, JOHN F., J. CHEM. SOC. CHEM. COMMUN.,(1989) N2, C. 761-762
  作者：HOUSTON, MICHAEL E. (JR)、HONEK, JOHN F.

  DOI：——

  日期：——
• TSUSHIMA, TADAHIKU;ISHIHARA, SHOICHI;FUJITA, YUSUKE, TETRAHEDRON LETT., 31,(1990) N1, C. 3017-3018
  作者：TSUSHIMA, TADAHIKU、ISHIHARA, SHOICHI、FUJITA, YUSUKE

  DOI：——

  日期：——
• TSUSIMA, TADAXIKO;ISIXARA, TEHRUITI
  作者：TSUSIMA, TADAXIKO、ISIXARA, TEHRUITI

  DOI：——

  日期：——