2'-deoxy-3',5'-bis-O-(tert-butyldiphenylsilyl)guanosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2'-deoxy-3',5'-bis-O-(tert-butyldiphenylsilyl)guanosine
• 英文别名: 2'-deoxy-3',5'-O-bis(tert-butyldiphenylsilyl)-guanosine；2-amino-9-[(2R,4S,5R)-4-[tert-butyl(diphenyl)silyl]oxy-5-[[tert-butyl(diphenyl)silyl]oxymethyl]oxolan-2-yl]-1H-purin-6-one
• 化学式: C₄₂H₄₉N₅O₄Si₂
• 分子量: 744.053
• InChiKey: ZCJIFYYGWVEVMR-LIVOIKKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  53
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1Z)-2-偶氮基-3-氧代-1,3-二苯基-1-丙烯-1-醇 、 2'-deoxy-3',5'-bis-O-(tert-butyldiphenylsilyl)guanosine 以 苯 为溶剂， 反应 3.0h， 以58%的产率得到
  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

文献信息

• Guanine Specific DNA Cleavage by Photoirradiation of Dibenzoyldiazomethane−Oligonucleotide Conjugates
  作者：Kazuhiko Nakatani、Junya Shirai、Shinsuke Sando、Isao Saito

  DOI：10.1021/ja970598j

  日期：1997.8.1

  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.