{4-[4-(3-Oxo-3-phenyl-propionyl)-benzoylamino]-butyl}-carbamic acid tert-butyl ester | 194040-98-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: {4-[4-(3-Oxo-3-phenyl-propionyl)-benzoylamino]-butyl}-carbamic acid tert-butyl ester
• CAS: 194040-98-7
• 化学式: C₂₅H₃₀N₂O₅
• 分子量: 438.524
• InChiKey: OUPACFUJPMSQHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  101.57
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  {4-[4-(3-Oxo-3-phenyl-propionyl)-benzoylamino]-butyl}-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Dibenzoyldiazomethane-acridine conjugate: A novel DNA photofootprinting agent

  摘要：

  Dibenzoyldiazomethane derivative covalently attached to acridine effectively cleaves DNA by photoirradiation with long wavelength UV light (> 400 nm). DNA cleavage experiments using P-32-5'-end-labeled DNA showed that the cleavage by the conjugate is neither sequence nor base selective, indicating that DBDM-acridine conjugate can be used as a photofootprinting agent. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01357-9
• 作为产物：
  描述：

  methyl 4-(3-oxo-3-phenylpropanoyl)benzoate 在 lithium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 {4-[4-(3-Oxo-3-phenyl-propionyl)-benzoylamino]-butyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Guanine Specific DNA Cleavage by Photoirradiation of Dibenzoyldiazomethane−Oligonucleotide Conjugates

  摘要：

  Photoirradiation of dibenzoyldiazomethane (DBDM) produced highly electrophilic benzoylketene via Wolff rearrangement. DBDM derivative possessing an aminoalkyl side chain induced a DNA cleavage selectively at guanine (G) residues upon photoirradiation and subsequent piperidine treatment. In order to devise photochemical DNA cleavers that can specifically alkylate a guanine residue proximal to the target sequence of long DNA fragments, a new reagent, DBDM-OSu, which facilitates the connection of DBDM unit to various DNA binders, was developed. DBDM-oligonucleotide (ODN) conjugates 5 and 6 were obtained by the coupling of 5'-aminohexyl 8-mer [H2N(CH2)(6)-d(ACGTCAGG)-3'] and 15-mer [H2N-(CH2)(6)-d(ACGTCAGGTGGCACT)-3'], respectively, with DBDM-OSu in aqueous acetonitrile in the presence of sodium bicarbonate. Photoirradiation of 5 and 6 in the presence of 25-mer 5'-d(AGTGCCACCTGACGTCTG(18)CTCTCTC)-3' having a complementary sequence induced cross-linking of both oligomers. A distinct cleavage band at guanine residue (G(18)) was observed upon heating the cross-linked oligomers with piperidine. A similar DNA cleavage reaction of 5'-d(AGTGCCACCTGACG(14)TG(16)CG(18)TG(20)CG(22)-TCT)-3' having multiple guanine sites in the presence of DBDM-ODN conjugate 6 indicated that the most effectively cleaved site is G(16). These results demonstrated that DBDM-oligonucleotide conjugates can serve as a new class of photonucleases that can cleave single-stranded DNA at predetermined guanine sites. Furthermore, the reagent DBDM-OSu can be used as a convenient and effective photoinducible electrophile for the cross-linking or the modification of biopolymers.

  DOI：

  10.1021/ja970598j