4-(2-diazo-3-phenyl-1,3-propanedion-1-yl)-phenylmethyl N-hydroxysuccinimidyl carbonate | 194040-91-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-(2-diazo-3-phenyl-1,3-propanedion-1-yl)-phenylmethyl N-hydroxysuccinimidyl carbonate
• 英文别名: [4-(2-Diazo-3-oxo-3-phenylpropanoyl)phenyl]methyl (2,5-dioxopyrrolidin-1-yl) carbonate
• CAS: 194040-91-0
• 化学式: C₂₁H₁₅N₃O₇
• 分子量: 421.366
• InChiKey: UMTQVADPEBYZFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  D-苯丙氨酸乙酯盐酸盐 、 4-(2-diazo-3-phenyl-1,3-propanedion-1-yl)-phenylmethyl N-hydroxysuccinimidyl carbonate 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以99%的产率得到(R)-2-[4-(2-Diazo-3-oxo-3-phenyl-propionyl)-benzyloxycarbonylamino]-3-phenyl-propionic acid ethyl 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
• 作为产物：
  描述：

  1-(4-hydroxymethylphenyl)-3-phenyl-1,3-propandione 在 2,6-二甲基吡啶 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 4-(2-diazo-3-phenyl-1,3-propanedion-1-yl)-phenylmethyl N-hydroxysuccinimidyl carbonate
  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