N-(triphenylmethyl)-D-phenylglycine | 124620-57-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-(triphenylmethyl)-D-phenylglycine
• 英文别名: (2R)-2-phenyl-2-(tritylamino)acetic acid
• CAS: 124620-57-1
• 化学式: C₂₇H₂₃NO₂
• 分子量: 393.485
• InChiKey: ILSKQVPSOSFJKL-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(triphenylmethyl)-D-phenylglycine 以60%的产率得到
  参考文献：
  名称：

  DOLENCE, E. KURT.;LIN, CHIA-EN;MILLER, MARVIN J.;PAYNE, SHELLEY M., J. MED. CHEM., 34,(1991) N, C. 956-968

  摘要：

  DOI：
• 作为产物：
  描述：

  左旋苯甘氨酸 、 三苯基氯甲烷 在 三甲基氯硅烷 、 三乙胺 作用下， 生成 N-(triphenylmethyl)-D-phenylglycine
  参考文献：
  名称：

  Synthesis and siderophore activity of albomycin-like peptides derived from N5-acetyl-N5-hydroxy-L-ornithine

  摘要：

  N5-Acetyl-N5-hydroxy-L-ornithine (1), the key constituent of several microbial siderophores, has been synthesized in 23 % yield overall from N-Cbz-L-glutamic acid 1-tert-butyl ester (6) derived from L-glutamic acid. Reduction of 6 to 7 and treatment with N-[(trichloroethoxy)carbonyl]-O-benzylhydroxylamine (8), and diethyl azodicarboxylate and triphenylphosphine followed by deprotection produced the protected N5-acetyl-N5-hydroxy-L-ornithine derivatives 11 and 12 in large quantities (10-20 g). Following alpha-amino and alpha-carboxyl deprotections of 11 and 12, EEDQ [2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline] mediated peptide coupling and final deprotection provided amino acid 1 and six albomycin-like peptides (20, 23, 25, 28, 35, and 36). The growth-promoting ability of each was evaluated with the siderophore biosynthesis mutant Shigella flexneri SA240 (SA 100 iucD:Tn5). These results indicate that substantial modification of the framework of peptide-based siderophores can be tolerated by microbial iron-transport systems.

  DOI：

  10.1021/jm00107a013

文献信息

• N5-Acetyl-N5-hydroxy-L-ornithine-derived siderophore-carbacephalosporin .beta.-lactam conjugates: iron transport mediated drug delivery
  作者：E. Kurt Dolence、Albert A. Minnick、Marvin J. Miller

  DOI：10.1021/jm00164a001

  日期：1990.2
• Synthesis and siderophore and antibacterial activity of N5-acetyl-N5-hydroxyl-L-ornithine derived siderophore-.beta.-lactam conjugates: iron transport mediated drug delivery
  作者：E. Kurt Dolence、Albert A. Minnick、Chia En Lin、Marvin J. Miller、Shelley M. Payne

  DOI：10.1021/jm00107a014

  日期：1991.3

  N5-Acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithyl-N5-acetyl-N5-hydroxy-L-ornithine, the functionally instrumental component of the albomycins and ferrichromes, has been incorporated as a ''carrier'' substructure into both carbacephalosporin and oxamazin type beta-lactam antibiotics. The previously synthesized protected version of this tripeptide (14) was coupled with various beta-lactam analogues 17, 19, 24, and 25 to give protected conjugates 21, 22, 26, and 27. Final deprotection by hydrogenolysis provided the deprotected siderophore-beta-lactam antibiotic conjugates 1-4. The growth-promoting ability of each has been evaluated using either the siderophore-deficient mutant Shigella flexneri SA 100 or S. flexneri SA240 (SA 100 iucD:Tn5). Measurement of the growth-promoting activity using two isogenic Escherichia coli strains differing only in the presence or absence of fhuA (hydroxamate ferrichrome receptor) suggests uptake by the hydroxamate iron-transport system. The antibacterial activity of these conjugates has been investigated, and the potential for use of the ferrichrome iron-transport system as a means of drug delivery is discussed.