2'-脱氧鸟苷3’,5’-二丁酸酯 | 79971-08-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 2'-脱氧鸟苷3’,5’-二丁酸酯
• 英文名称: 3',5'-O-dibutyryl 2'-deoxyguanosine
• 英文别名: 2'-deoxyguanosine 3',5'-dibutyrate；[(2R,3S,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3-butanoyloxyoxolan-2-yl]methyl butanoate；[(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-butanoyloxyoxolan-2-yl]methyl butanoate
• CAS: 79971-08-7
• 化学式: C₁₈H₂₅N₅O₆
• 分子量: 407.426
• InChiKey: QKYJOTXTRCUHCM-QJPTWQEYSA-N

物化性质

• 熔点：
  >250°C (dec.)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2'-脱氧鸟苷3’,5’-二丁酸酯 在 溶剂黄146 、 三乙胺 、 三苯基膦 、 sodium nitrite 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 5.25h， 生成 [(2R,3S,5R)-3-butanoyloxy-5-[6-[2-(4-nitrophenyl)ethoxy]-2-(trifluoromethylsulfonyloxy)purin-9-yl]oxolan-2-yl]methyl butanoate
  参考文献：
  名称：

  通过O 2-三氟甲磺酸-O 6 -NPE 2'-脱氧黄嘌呤的亚磷酰胺合成在鸟嘌呤N 2上含有大分子加合物的寡核苷酸

  摘要：

  已经通过后寡聚化策略制备了在鸟嘌呤N 2上带有大加合物的寡脱氧核苷酸，在该策略中，使含有高反应性O 2-三氟甲磺酰基-O 6-（对-硝基苯乙基）2'-脱氧黄嘌呤残基的寡核苷酸与（±）-10β-氨基反应-7,8,9,10-四氢苯并[ a ]py-7β，8α，9α-三醇及相关化合物。

  DOI：

  10.1016/s0040-4039(00)00461-5
• 作为产物：
  描述：

  丁酸酐 、 2'-脱氧鸟苷 在 吡啶 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 15.0h， 以42%的产率得到2'-脱氧鸟苷3’,5’-二丁酸酯
  参考文献：
  名称：

  Photochemical epoxidation of aflatoxin B1 and sterigmatocystin: synthesis of guanine-containing adducts

  摘要：

  DOI：

  10.1021/ja00366a029

文献信息

• Unraveling the Aflatoxin−FAPY Conundrum:  Structural Basis for Differential Replicative Processing of Isomeric Forms of the Formamidopyrimidine-Type DNA Adduct of Aflatoxin B₁
  作者：Kyle L. Brown、James Z. Deng、Rajkumar S. Iyer、Lalitha G. Iyer、Markus W. Voehler、Michael P. Stone、Constance M. Harris、Thomas M. Harris

  DOI：10.1021/ja063781y

  日期：2006.11.1

  Aflatoxin B-1 (AFB) epoxide forms an unstable N7 guanine adduct in DNA. The adduct undergoes base-catalyzed ring opening to give a highly persistent formamidopyrimidine (FAPY) adduct which exists as a mixture of forms. Acid hydrolysis of the FAPY adduct gives the FAPY base which exists in two separable but interconvertible forms that have been assigned by various workers as functional, positional, or conformational isomers. Recently, this structural question became important when one of the two major FAPY species in DNA was found to be potently mutagenic and the other a block to replication [Smela, M. E.; Hamm, M. L.; Henderson, P. T.; Harris, C. M.; Harris, T. M.; Essigmann, J.M. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 6655-6660]. NMR studies carried out on the AFB-FAPY bases and deoxynucleoside 3',5'-dibutyrates now establish that the separable FAPY bases and nucleosides are diastereomeric N-5 formyl derivatives involving axial asymmetry around the congested pyrimidine C5-N-5 bond. Anomerization of the protected beta-deoxyriboside was not observed, but in the absence of acyl protection, both anomerization and furanosyl -> pyranosyl ring expansion occurred. In oligodeoxynucleotides, two equilibrating FAPY species, separable by HPLC, are assigned as anomers. The form normally present in duplex DNA is the mutagenic species. It has previously been assigned as the, anomer by NMR (Mao, H.; Deng, Z. W.; Wang, F.; Harris, T. M.; Stone, M. P. Biochemistry 1998, 37, 4374-4387). In single-stranded environments the dominant species is the R anomer; it is a block to replication.
• ACYL DEOXYRIBONUCLEOSIDE DERIVATIVES AND USES THEREOF
  申请人：PRO-NEURON, INC.

  公开号：EP0355131B1

  公开（公告）日：1996-09-04
• Photochemical epoxidation of aflatoxin B1 and sterigmatocystin: synthesis of guanine-containing adducts
  作者：George Buechi、Kerry W. Fowler、Alex M. Nadzan

  DOI：10.1021/ja00366a029

  日期：1982.1
• Synthesis of oligonucleotides containing bulky adducts at guanine N2 via the phosphoramidite of O2-triflate-O6-NPE 2′-deoxyxanthosine
  作者：Monica D Cooper、Richard P Hodge、Pamela J Tamura、Amanda S Wilkinson、Constance M Harris、Thomas M Harris

  DOI：10.1016/s0040-4039(00)00461-5

  日期：2000.5

  Oligodeoxynucleotides bearing bulky adducts at guanine N2 have been prepared by a postoligomerization strategy in which oligonucleotides containing a highly reactive O2-trifluoromethanesulfonyl-O6-(p-nitrophenethyl) 2′-deoxyxanthosine residue were reacted with (±)-10β-amino-7,8,9,10-tetrahydro-benzo[a]pyrene-7β,8α,9α-triol and related compounds.

  已经通过后寡聚化策略制备了在鸟嘌呤N 2上带有大加合物的寡脱氧核苷酸，在该策略中，使含有高反应性O 2-三氟甲磺酰基-O 6-（对-硝基苯乙基）2'-脱氧黄嘌呤残基的寡核苷酸与（±）-10β-氨基反应-7,8,9,10-四氢苯并[ a ]py-7β，8α，9α-三醇及相关化合物。