(1S,2R,3R,4S)-1-[9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylamino]-1,2,3,4-tetrahydro-benzo[a]anthracene-2,3,4-triol | 130195-42-5

• 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: (1S,2R,3R,4S)-1-[9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylamino]-1,2,3,4-tetrahydro-benzo[a]anthracene-2,3,4-triol
• 英文别名: Adenosine, 2'-deoxy-N-(1,2,3,4-tetrahydro-2,3,4-trihydroxybenz(a)anthracen-1-yl)-, (1S-(1alpha,2beta,3alpha,4beta))-；(1S,2R,3R,4S)-1-[[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]-1,2,3,4-tetrahydrobenzo[a]anthracene-2,3,4-triol
• CAS: 130195-42-5
• 化学式: C₂₈H₂₇N₅O₆
• 分子量: 529.552
• InChiKey: FPWMJTSJTLVDAW-DSDAIYBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  39
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (1S,2R,3R,4S)-1-[9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylamino]-1,2,3,4-tetrahydro-benzo[a]anthracene-2,3,4-triol 在 吡啶 作用下， 生成 Acetic acid (1S,2R,3R,4S)-3,4-diacetoxy-1-[9-((2R,4S,5R)-4-acetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylamino]-1,2,3,4-tetrahydro-benzo[a]anthracen-2-yl ester
  参考文献：
  名称：

  Structures of covalent nucleoside adducts formed from adenine, guanine, and cytosine bases of DNA and the optically active bay-region 3,4-diol 1,2-epoxides of benz[a]anthracene

  摘要：

  Chemical structures of the principal covalent adducts formed from DNA upon reaction in vitro with the four optically active 3,4-diol 1,2-epoxides of benz[a]anthracene have been elucidated at the nucleoside level. In addition to adducts formed by cis and trans addition of the exocyclic amino groups of deoxyadenosine (dA) and deoxyguanosine (dG) and a trans deoxycytidine (dC) adduct, chemical characterization of a deglycosylated N-7 dG adduct formed in DNA by trans opening of the (4S,3R)-diol (2R,1S)-epoxide isomer is reported. Relative stereochemistries of the adducts (cis versus trans opening of the epoxides by the exocyclic amino groups) were deduced from the coupling constants of the methine protons of the tetrahydro benzo rings of the acetylated derivatives. Adducts having (S)-configuration at the attachment site on the hydrocarbon moiety have CD spectra that exhibit a positive band at 250-260 nm and a negative band at longer wavelengths, whereas (R)-configuration at this center gives rise to CD spectra with bands of approximately equal intensity and opposite sign. This allowed assignment of cis versus trans addition to the chiral epoxides for adducts that were not generated in sufficient quantity to obtain NMR spectra. Analysis of the patterns of adducts derived from benz[a]anthracene, benzo[c]phenanthrene, and benzo[a]pyrene shows that the comparative tumorigenicities of the diol epoxide isomers of each hydrocarbon do not correlate well with the extent of adduct formation, the ratio of cis versus trans addition to the epoxide, the propensity for forming adducts at dC or the N-7 position of dG, or the ratio of adduct formation at dA versus dG, although tumorigenicity may correlate with the ability to form dG adducts with (S)-configuration at the N-substituted benzylic carbon, especially those arising from trans addition to the epoxide.

  DOI：

  10.1021/jo00067a039
• 作为产物：
  描述：

  (+)-(1R,2S,3R,4S)-3,4-Dihydroxy-1,2-epoxy-1,2,3,4-tetrahydrobenz(a)anthracene 、 2'-脱氧腺苷-5'-单磷酸 生成 (1S,2R,3R,4S)-1-[9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylamino]-1,2,3,4-tetrahydro-benzo[a]anthracene-2,3,4-triol 、 (1R,2R,3R,4S)-1-[9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ylamino]-1,2,3,4-tetrahydro-benzo[a]anthracene-2,3,4-triol
  参考文献：
  名称：

  Structures of covalent nucleoside adducts formed from adenine, guanine, and cytosine bases of DNA and the optically active bay-region 3,4-diol 1,2-epoxides of benz[a]anthracene

  摘要：

  Chemical structures of the principal covalent adducts formed from DNA upon reaction in vitro with the four optically active 3,4-diol 1,2-epoxides of benz[a]anthracene have been elucidated at the nucleoside level. In addition to adducts formed by cis and trans addition of the exocyclic amino groups of deoxyadenosine (dA) and deoxyguanosine (dG) and a trans deoxycytidine (dC) adduct, chemical characterization of a deglycosylated N-7 dG adduct formed in DNA by trans opening of the (4S,3R)-diol (2R,1S)-epoxide isomer is reported. Relative stereochemistries of the adducts (cis versus trans opening of the epoxides by the exocyclic amino groups) were deduced from the coupling constants of the methine protons of the tetrahydro benzo rings of the acetylated derivatives. Adducts having (S)-configuration at the attachment site on the hydrocarbon moiety have CD spectra that exhibit a positive band at 250-260 nm and a negative band at longer wavelengths, whereas (R)-configuration at this center gives rise to CD spectra with bands of approximately equal intensity and opposite sign. This allowed assignment of cis versus trans addition to the chiral epoxides for adducts that were not generated in sufficient quantity to obtain NMR spectra. Analysis of the patterns of adducts derived from benz[a]anthracene, benzo[c]phenanthrene, and benzo[a]pyrene shows that the comparative tumorigenicities of the diol epoxide isomers of each hydrocarbon do not correlate well with the extent of adduct formation, the ratio of cis versus trans addition to the epoxide, the propensity for forming adducts at dC or the N-7 position of dG, or the ratio of adduct formation at dA versus dG, although tumorigenicity may correlate with the ability to form dG adducts with (S)-configuration at the N-substituted benzylic carbon, especially those arising from trans addition to the epoxide.

  DOI：

  10.1021/jo00067a039

文献信息

• Structures of covalent nucleoside adducts formed from adenine, guanine, and cytosine bases of DNA and the optically active bay-region 3,4-diol 1,2-epoxides of benz[a]anthracene
  作者：Albert M. Cheh、Anju Chadha、Jane M. Sayer、Herman J. C. Yeh、Haruhiko Yagi、Lewis K. Pannell、Donald M. Jerina

  DOI：10.1021/jo00067a039

  日期：1993.7

  Chemical structures of the principal covalent adducts formed from DNA upon reaction in vitro with the four optically active 3,4-diol 1,2-epoxides of benz[a]anthracene have been elucidated at the nucleoside level. In addition to adducts formed by cis and trans addition of the exocyclic amino groups of deoxyadenosine (dA) and deoxyguanosine (dG) and a trans deoxycytidine (dC) adduct, chemical characterization of a deglycosylated N-7 dG adduct formed in DNA by trans opening of the (4S,3R)-diol (2R,1S)-epoxide isomer is reported. Relative stereochemistries of the adducts (cis versus trans opening of the epoxides by the exocyclic amino groups) were deduced from the coupling constants of the methine protons of the tetrahydro benzo rings of the acetylated derivatives. Adducts having (S)-configuration at the attachment site on the hydrocarbon moiety have CD spectra that exhibit a positive band at 250-260 nm and a negative band at longer wavelengths, whereas (R)-configuration at this center gives rise to CD spectra with bands of approximately equal intensity and opposite sign. This allowed assignment of cis versus trans addition to the chiral epoxides for adducts that were not generated in sufficient quantity to obtain NMR spectra. Analysis of the patterns of adducts derived from benz[a]anthracene, benzo[c]phenanthrene, and benzo[a]pyrene shows that the comparative tumorigenicities of the diol epoxide isomers of each hydrocarbon do not correlate well with the extent of adduct formation, the ratio of cis versus trans addition to the epoxide, the propensity for forming adducts at dC or the N-7 position of dG, or the ratio of adduct formation at dA versus dG, although tumorigenicity may correlate with the ability to form dG adducts with (S)-configuration at the N-substituted benzylic carbon, especially those arising from trans addition to the epoxide.