8,5'-O-cycloguanosine | 74227-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 8,5'-O-cycloguanosine
• 英文别名: (1R,13R,14S,15R)-5-amino-14,15-dihydroxy-11,16-dioxa-2,4,6,9-tetrazatetracyclo[11.2.1.02,10.03,8]hexadeca-3(8),5,9-trien-7-one
• CAS: 74227-98-8
• 化学式: C₁₀H₁₁N₅O₅
• 分子量: 281.228
• InChiKey: AYGCPRDWDFGNAA-UMMCILCDSA-N

物化性质

• 密度：
  2?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.29
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  148.51
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  8,5'-O-cycloguanosine 在 盐酸 作用下， 反应 8.0h， 生成 8-羟基鸟苷
  参考文献：
  名称：

  Kohda, Kohfuku; Baba, Kunihisa; Kawazoe, Yutaka, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 5, p. 2298 - 2301

  摘要：

  DOI：
• 作为产物：
  描述：

  鸟苷 生成 8,5'-O-cycloguanosine
  参考文献：
  名称：

  KOHDA, KOHFUKU;BABA, KUNIHISA;KAWAZOE, YUTAKA, 14TH SYMP. NUCL. ACIDS CHEM., TOKUSHIMA, OCT. 30TH - NOV. 1ST, 1986, OXFO+

  摘要：

  DOI：

文献信息

• Chemistry of the 8-Nitroguanine DNA Lesion: Reactivity, Labelling and Repair
  作者：Katie J. Alexander、Matthew McConville、Kathryn R. Williams、Konstantin V. Luzyanin、Ian A. O'Neil、Richard Cosstick

  DOI：10.1002/chem.201705541

  日期：2018.2.26

  nucleotides, despite the fact that their biological effects are closely linked to their chemical properties. To this end, a selection of chemical reactions have been performed on 8‐nitroguanine nucleosides and oligodeoxynucleotides. Reactions with alkylating reagents reveal how the 8‐nitro substituent affects the reactivity of the purine ring, by significantly decreasing the reactivity of the N2 position

  DNA中的8-硝基鸟嘌呤损伤越来越多地与炎症相关的癌变相关，而鸟苷3'，5'-环一磷酸的相同修饰在NO介导的信号转导中产生了第二个信使。尽管关于8-硝基鸟嘌呤核苷酸的生物学效应与其化学性质紧密相关，但对8-硝基鸟嘌呤核苷酸的化学知之甚少。为此，已对8-硝基鸟嘌呤核苷和寡脱氧核苷酸进行了化学反应选择。与烷基化试剂的反应揭示了8-硝基取代基如何通过显着降低N 2位置的反应性以及同时在N处的相对反应性而影响嘌呤环的反应性1似乎被增强。有趣的是，用硫醇置换硝基导致了标记该病灶的有效且特异性的方法，并在寡聚脱氧核苷酸中得到证实。另外，通过使用氢化物​​源的还原性脱硝作用，该病变的修复也被证明是化学上可行的反应。
• Formation and Reactions of <i>N</i>⁷-Aminoguanosine and Derivatives
  作者：F. Peter Guengerich、Ralf G. Mundkowski、Markus Voehler、Fred F. Kadlubar

  DOI：10.1021/tx990094u

  日期：1999.10.1

  Arylamines are mutagens and carcinogens and are thought to initiate tumors by forming adducts with DNA. The major adducts are C-8-guanyl, and we have previously suggested a role for guanyl-N-7 intermediates in the formation process. N-7-Aminoguanosine (Guo) was synthesized and characterized, with the position of the NH2 at N7 established by two-dimensional rotating frame Overhauser enhancement NMR spectroscopy. In DMF, N-7-NH(2)Guo formed C-8-NH(2)Guo and the cyclic product C-8:5'-O-cycloGuo. In aqueous media, these products were formed along with 8-oxo-7,8-dihydroGuo, N-7-NH(2)guanine, and a product characterized as a purine 8,9-ring-opened derivative (N-aminoformamidopyrimidine). The rate of aqueous decomposition of N-7-NH(2)Guo increased with pH, with a t(1/2) of 10 h at pH 7 and a t(1/2) of 2 h at pH 9. The rate of migration of NH2 from N7 to C8 is fast enough to explain the formation of C-8-NH(2)Guo from the reaction of 2,4-dinitrophenoxyamine with Guo but not the formation of C-8-(arylamino)Guo in the reaction of Guo with aryl hydroxylamine esters; however, the fluorenyl moiety may facilitate the proposed rearrangement by stabilizing an incipient negative charge in the transfer. In the reaction of Guo with N-hydroxy-2-aminofluorene and acetylsalicylic acid, a peak with the mass spectrum expected for N-7-(2-aminofluorenyl)Guo was detected early in the reaction and was distinguished from C-8-(2-aminofluorenyl)Guo. NMR experiments with [8-C-13]Guo also provided some additional support for transient formation of N-7-(2-aminofluorenyl)Guo. We conclude that a guanyl-N-7 intermediate is reasonable in the reaction of activated arylamines with nucleic acids, although an exact rate of transfer of an N-7-arylamine group to the C8 position has not yet been quantified. The results provide an explanation for the numerous products associated with modification of DNA by activate arylamines. However, the contribution of "direct" reaction at the guanine C8 atom cannot be excluded.
• KOHDA, KOHFUKU;BABA, KUNIHISA;KAWAZOE, YUTAKA, TETRAHEDRON, 46,(1990) N, C. 1531-1540
  作者：KOHDA, KOHFUKU、BABA, KUNIHISA、KAWAZOE, YUTAKA

  DOI：——

  日期：——