1-<5'-<(phenylalanyl-Δ^Z-dehydrophenylalanyl)amino>-5'-deoxy-β-D-allofuranosyluronic acid>uracil | 100995-69-5

• 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: 1-<5'-<(phenylalanyl-Δ^Z-dehydrophenylalanyl)amino>-5'-deoxy-β-D-allofuranosyluronic acid>uracil
• CAS: 100995-69-5
• 化学式: C₂₈H₂₉N₅O₉
• 分子量: 579.566
• InChiKey: VDTGAKGMDNPMAV-KVTJIGKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.55
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  226.07
• 氢给体数：
  7.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  (S)-[(E)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionylamino)-3-phenyl-acryloylamino]-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid 在 氢溴酸 、 溶剂黄146 作用下， 反应 0.5h， 生成 1-<5'-<(phenylalanyl-Δ^Z-dehydrophenylalanyl)amino>-5'-deoxy-β-D-allofuranosyluronic acid>uracil
  参考文献：
  名称：

  Synthesis and biological properties of chitin synthetase inhibitors resistant to cellular peptidases

  摘要：

  The synthesis and biological properties of seven polyoxins (4-10) designed to avoid peptidase hydrolysis in Candida albicans are presented. Five dipeptidyl and two tripeptidyl polyoxin analogues were synthesized by coupling an amino acid active ester or azlactone to uracil polyoxin C (2) or polyoxin D (1), subsequent removal of the protecting group, and purification by preparative HPLC. A new and novel route for introducing an n-propyl group onto the alpha-amino group of peptides is reported. With the exception of a carboxamide derivative, 8, all analogues were resistant to hydrolysis by a cell extract or permeabilized cells of Candida. Chitin synthetase inhibition constants were determined for 4-10 and the KI values ranged from 7.15 X 10(-6) M for octanoyl-phenylalanyl-polyoxin D (10) to 1.06 X 10(-3) M for D-tryptophanyl-uracil polyoxin C (6). These novel polyoxins do not compete with the transport of either peptides or uridine into the cell. Millimolar concentrations of compounds 4-10 are required to inhibit growth, cause morphological alterations, or reduce the viability of C. albicans.

  DOI：

  10.1021/jm00155a034