L-m-FPhe-L-Ala | 87184-20-1

• 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-m-FPhe-L-Ala
• 英文别名: (2S)-2-[[(2S)-2-amino-3-(3-fluorophenyl)propanoyl]amino]propanoic acid
• CAS: 87184-20-1
• 化学式: C₁₂H₁₅FN₂O₃
• 分子量: 254.261
• InChiKey: KFBSGKGCCTYHEQ-XVKPBYJWSA-N

物化性质

• 沸点：
  502.5±50.0 °C(Predicted)
• 密度：
  1.287±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Phenyl-1-(2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl)ethanamine;hydrochloride 、 L-m-FPhe-L-Ala 在 N-甲基吗啉 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  含α-氨基硼的拟肽的合成及其抗菌活性。

  摘要：

  已合成了175个包含α-氨基硼酸或硼酸酯的二肽模拟物和三肽模拟物的文库，并筛选了其对结核分枝杆菌，白色念珠菌，金黄色葡萄球菌，化脓性链球菌，大肠杆菌和铜绿假单胞菌的活性。尽管没有明确的构效关系，但几种化合物对不同病原体表现出有希望的活性。版权所有©2013欧洲多肽协会和John Wiley＆Sons，Ltd.

  DOI：

  10.1002/psc.2583
• 作为产物：
  描述：

  Cbz-L-m-FPhe-L-Ala-OBzl 在 palladium on activated charcoal 甲醇 、 环己烯 作用下， 反应 3.0h， 以75%的产率得到L-m-FPhe-L-Ala
  参考文献：
  名称：

  Transport of antimicrobial agents using peptide carrier systems: anticandidal activity of m-fluorophenylalanine-peptide conjugates

  摘要：

  A series of di- and tripeptides containing D- and L-m-fluorophenylalanine was prepared and tested in vitro for the ability to inhibit the growth of the yeast Candida albicans. The results demonstrate that peptides containing L-m-fluorophenylalanine inhibited the growth of C. albicans with minimum inhibitory concentrations (MIC's) ranging from 0.5 to 63 micrograms/mL. The parent L-m-fluorophenylalanine and peptides containing D-m-fluorophenylalanine were inactive (MIC greater than 250 micrograms/mL) in these tests. The results of competitive antagonism studies support peptide transport mediated entry of the inhibitory peptides, followed by release of L-m-fluorophenylalanine inside the cell.

  DOI：

  10.1021/jm00366a013

文献信息

• Transport of antimicrobial agents using peptide carrier systems: anticandidal activity of m-fluorophenylalanine-peptide conjugates
  作者：William D. Kingsbury、Jeffrey C. Boehm、Rajanikant J. Mehta、Sarah F. Grappel

  DOI：10.1021/jm00366a013

  日期：1983.12

  A series of di- and tripeptides containing D- and L-m-fluorophenylalanine was prepared and tested in vitro for the ability to inhibit the growth of the yeast Candida albicans. The results demonstrate that peptides containing L-m-fluorophenylalanine inhibited the growth of C. albicans with minimum inhibitory concentrations (MIC's) ranging from 0.5 to 63 micrograms/mL. The parent L-m-fluorophenylalanine and peptides containing D-m-fluorophenylalanine were inactive (MIC greater than 250 micrograms/mL) in these tests. The results of competitive antagonism studies support peptide transport mediated entry of the inhibitory peptides, followed by release of L-m-fluorophenylalanine inside the cell.
• Synthesis and antimicrobial activity of <i>α</i> -aminoboronic-containing peptidomimetics
  作者：Olga V. Gozhina、John Sigurd Svendsen、Tore Lejon

  DOI：10.1002/psc.2583

  日期：2014.1

  tripeptidomimetics containing an α‐amino boronic acid or boronate has been synthesized, and the activity toward Mycobacterium tuberculosis, Candida albicans, Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli and Pseudomonas aeruginosa has been screened. Although there is no clear structure–activity relationship, several compounds exhibit promising activity against different pathogens. Copyright

  已合成了175个包含α-氨基硼酸或硼酸酯的二肽模拟物和三肽模拟物的文库，并筛选了其对结核分枝杆菌，白色念珠菌，金黄色葡萄球菌，化脓性链球菌，大肠杆菌和铜绿假单胞菌的活性。尽管没有明确的构效关系，但几种化合物对不同病原体表现出有希望的活性。版权所有©2013欧洲多肽协会和John Wiley＆Sons，Ltd.