3-(2-deoxy-β-D-erythro-pentofuranosyl)-5,6,7,8-tetrahydro-8-(N2-deoxyguanosinyl)-pyrimido[1,2-α]purin-10(3H)-one | 382591-27-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 3-(2-deoxy-β-D-erythro-pentofuranosyl)-5,6,7,8-tetrahydro-8-(N2-deoxyguanosinyl)-pyrimido[1,2-α]purin-10(3H)-one
• 英文别名: 3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-[[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-1H-purin-2-yl]amino]-5,6,7,8-tetrahydropyrimido[1,2-a]purin-10-one
• CAS: 382591-27-7
• 化学式: C₂₃H₂₈N₁₀O₈
• 分子量: 572.538
• InChiKey: XAMIIFSNZFCDAG-HONWHVAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  233
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-(2-deoxy-β-D-erythro-pentofuranosyl)-5,6,7,8-tetrahydro-8-(N2-deoxyguanosinyl)-pyrimido[1,2-α]purin-10(3H)-one 在 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 以75%的产率得到1,3-bis(2'-deoxyguanosin-N2-yl)propane
  参考文献：
  名称：

  Interchain Cross-Linking of DNA Mediated by the Principal Adduct of Acrolein

  摘要：

  A DNA duplex containing the primary acrolein adduct, 3-(2-deoxy-beta -D-erythro-pentofuranosyl)-5,6,7,8-tetrahydro-8-hydroxypyrimido[1,2-a]purin-10(3H)-one (2), of deoxyguanosine in a 5'-CpG sequence context spontaneously but reversibly formed an interchain cross-link with the exocyclic amino group of deoxyguanosine in the opposing chain. The linkage was sufficiently stable that the cross-linked duplex could be isolated by HPLC and characterized by MALDI-TOF mass spectrometry. Enzymatic degradation gave his-nucleoside 6, which was independently prepared by direct reaction of 2 with dGuo.

  DOI：

  10.1021/tx010127h
• 作为产物：
  描述：

  2'-脱氧鸟苷 、 3H-8-hydroxy-3-(β-D-2′-deoxyribofuranosyl)-5,6,7,8-tetrahydropyrido[3,2-a]purine-9-one 以 二甲基亚砜 为溶剂， 反应 120.0h， 以65%的产率得到3-(2-deoxy-β-D-erythro-pentofuranosyl)-5,6,7,8-tetrahydro-8-(N2-deoxyguanosinyl)-pyrimido[1,2-α]purin-10(3H)-one
  参考文献：
  名称：

  Interchain Cross-Linking of DNA Mediated by the Principal Adduct of Acrolein

  摘要：

  A DNA duplex containing the primary acrolein adduct, 3-(2-deoxy-beta -D-erythro-pentofuranosyl)-5,6,7,8-tetrahydro-8-hydroxypyrimido[1,2-a]purin-10(3H)-one (2), of deoxyguanosine in a 5'-CpG sequence context spontaneously but reversibly formed an interchain cross-link with the exocyclic amino group of deoxyguanosine in the opposing chain. The linkage was sufficiently stable that the cross-linked duplex could be isolated by HPLC and characterized by MALDI-TOF mass spectrometry. Enzymatic degradation gave his-nucleoside 6, which was independently prepared by direct reaction of 2 with dGuo.

  DOI：

  10.1021/tx010127h

文献信息

• Interchain Cross-Linking of DNA Mediated by the Principal Adduct of Acrolein
  作者：Ivan D. Kozekov、Lubomir V. Nechev、Ana Sanchez、Constance M. Harris、R. Stephen Lloyd、Thomas M. Harris

  DOI：10.1021/tx010127h

  日期：2001.11.1

  A DNA duplex containing the primary acrolein adduct, 3-(2-deoxy-beta -D-erythro-pentofuranosyl)-5,6,7,8-tetrahydro-8-hydroxypyrimido[1,2-a]purin-10(3H)-one (2), of deoxyguanosine in a 5'-CpG sequence context spontaneously but reversibly formed an interchain cross-link with the exocyclic amino group of deoxyguanosine in the opposing chain. The linkage was sufficiently stable that the cross-linked duplex could be isolated by HPLC and characterized by MALDI-TOF mass spectrometry. Enzymatic degradation gave his-nucleoside 6, which was independently prepared by direct reaction of 2 with dGuo.