9-(α-D-arabinofuranosyl)guanine | 34793-16-3

• 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: 9-(α-D-arabinofuranosyl)guanine
• 英文别名: 2-Amino-9-((2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one；2-amino-9-[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 34793-16-3
• 化学式: C₁₀H₁₃N₅O₅
• 分子量: 283.244
• InChiKey: NYHBQMYGNKIUIF-ICKFSKTQSA-N

物化性质

• 熔点：
  210 °C (decomp)
• 沸点：
  775.9±70.0 °C(Predicted)
• 密度：
  2.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-(α-D-arabinofuranosyl)guanine 、 异丁酸酐 在 吡啶 、 三甲基氯硅烷 、 氨 作用下， 以 水 为溶剂， 反应 2.75h， 以75%的产率得到9-(α-D-arabinofuranosyl)-2-N-isobutyrylguanine
  参考文献：
  名称：

  α-构型阿拉伯核酸的合成和杂交研究†

  摘要：

  四个天然碱的α-L-阿拉伯糖和α-D-阿拉伯糖构型的呋喃呋喃糖基核苷的合成[胸腺嘧啶 （一只老鼠）， 腺嘌呤 （ara-A）， 胞嘧啶 （ara-C） 和 鸟嘌呤（ara-G）]与含有α-L-ara-T和-A，α-D-ara-T和-A以及2'-氨基-α-L-ara-T的寡核苷酸的杂交特性一起报道。单体。2' - O-乙酰化的α-L-ara-T，-A，-C和-G，α-D-ara-T，-A，-C和-G和N2'-酰化的α-L-合成了ara-T亚磷酰胺结构单元，并将其与标准DNA亚磷酰胺一起用于18-mer寡核苷酸的固相合成。热变性实验表明，掺入了三到六种阿拉伯糖-配置成DNA-寡核苷酸的单体降低了对反平行DNA / RNA补体的结合亲和力。完全修饰的α-L-ara-寡核苷酸不与DNA / RNA互补序列杂交，而证实了完全修饰的α-D-ara-寡核苷酸与互补DNA / RNA在平行链方向上的杂交。

  DOI：

  10.1039/b905019c
• 作为产物：
  描述：

  鸟嘌呤 在 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 、 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成 9-(α-D-arabinofuranosyl)guanine
  参考文献：
  名称：

  Biocatalytic Separation of N-7/N-9 Guanine Nucleosides

  摘要：

  Vorbruggen coupling of trimethylsilylated 2-N-isobutanoylguanine with peracetylated pentofuranose derivatives generally gives inseparable N-7/N-9 glycosyl mixtures We have shown that the two isomers can be separated biocatalytically by Novozyme-435-mediated selective deacetylation of the 5'-O-acetyl group of peracetylated N-9 guanine nucleosides

  DOI：

  10.1021/jo101565e

文献信息

• Nucleic Acid Related Compounds. 93. A Solution for the Historic Problem of Regioselective Sugar−Base Coupling To Produce 9-Glycosylguanines or 7-Glycosylguanines¹
  作者：Morris J. Robins、Ruiming Zou、Zhiqiang Guo、Stanislaw F. Wnuk

  DOI：10.1021/jo9617023

  日期：1996.1.1

  Per(trimethylsilyl)-2-N-acylguanine derivatives and tetra-O-acylpentofuranoses were coupled [tin-(IV) chloride or titanium(IV) chloride catalysis] to give predominant formation of 7-glycosylguanines. With TiCl4, a fortuitous organic/aqueous partitioning allowed isolation of 7-glycosylguanines from the 7/9 isomer mixtures. Per(trimethylsilyl)-2-N-acyl-6-O-(diphenylcarbamoyl)guanine derivatives and tetra-O-acylpentofuranoses underwent regioselective coupling (trimethylsilyl trifluoromethane-sulfonate catalysis) to give 9-glycosylguanines. The 6-O-(diphenylcarbamoyl)peracyl-9-beta-D-ribofuranosyl isomer was shown to be both the kinetic and thermodynamic coupling product. Deprotection of all of the peracyl coupling products was effected under mild conditions to give good to high yields of guanine nucleoside analogues. These methodologies provide solutions for the regioselective synthesis of 7- and 9-glycosylguanine nucleosides.
• Nucleotides. LXXIV Synthesis of a-D-Arabino-oligonucleotides
  作者：Christoph Henke、Wolfgang Pfleiderer

  DOI：10.1080/15257770500267113

  日期：2005.9.1

  The 5 alpha-D-arabinofuranosylnucleosides alpha-araU (15), alpha-araT (18), alpha-araC (22), alpha-araA (25), and alpha-araG (28) have been synthesized by the modified silyl-method. The amino groups at the nucleobases and the 2'-hydroxy group at the sugar moiety were protected by the 2-(4-nitro-phenyl) ethoxycarbonyl (npeoc) group (37-40) and the amide function in alpha-araG was additionally blocked by the 2-(4-nitrophenyl)ethyl group (63) to improve solubility in organic solvents. Mono-and dimethoxytritylation of the 5'-OH group was performed in the usual manner to give 41-48, 64, and 65 in high yields and further substitution of the 3'-OH group led to the monomeric building blocks 66-75 as well as the 3'-O-succinoyl derivatives 76-85 functioning as starting units in solid-support oligonucleotide synthesis. A large number of oligo-alpha-arabinonucleotides have been prepared on modified CPG-material applying the npeoc/npe strategy as a very efficient synthetic tool for highly purified, homogenous oligomers. Hybridizations between alpha-arabinonucleotide strands revealed in analogy to earlier findings an antiparallel orientation whereas the combination of an oligo-alpha-D-arabinonucleotide with a complementary oligo-2'-deoxy-beta-D-ribofuranosylnucleotide showed base-pairing only if a parallel polarity was present. The advantages in oligo-alpha-arabinonucleotide synthesis were furthermore demonstrated by the synthesis of the t alpha-ANA(his) a structural analog of the natural tRNA(his) of the phage T5.
• ZOU, RUIMING;ROBINS, MORRIS J., CAN. J. CHEM., 65,(1987) N 6, 1436-1437
  作者：ZOU, RUIMING、ROBINS, MORRIS J.

  DOI：——

  日期：——
• OLIGO(ALPHA-ARABINOFURANOSYL NUCLEOTIDES) AND ALPHA-ARABINOFURANOSYL PRECURSORS THEREOF
  申请人：MICROPROBE CORPORATION

  公开号：EP0543913A1

  公开（公告）日：1993-06-02
• EP0543913A4
  申请人：——

  公开号：EP0543913A4

  公开（公告）日：1995-10-04