2-N-(9-fluorenylmethoxycarbonyl)guanosine | 87424-18-8

• 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: 2-N-(9-fluorenylmethoxycarbonyl)guanosine
• 英文别名: 9H-fluoren-9-ylmethyl N-[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-1H-purin-2-yl]carbamate
• CAS: 87424-18-8
• 化学式: C₂₅H₂₃N₅O₇
• 分子量: 505.487
• InChiKey: GTQZMIUKGUFZFU-ZDXOVATRSA-N

物化性质

• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  168
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-N-(9-fluorenylmethoxycarbonyl)guanosine 在 ammonium hydroxide 作用下， 以 吡啶 为溶剂， 反应 0.5h， 生成 鸟苷
  参考文献：
  名称：

  Heikkilae, Jarmo; Chattopadhyaya, Jyoti, Heterocycles, 1984, vol. 21, # 2, p. 542

  摘要：

  DOI：
• 作为产物：
  描述：

  9H-fluoren-9-ylmethyl N-[9-[(2R,3R,4R,5R)-3,4-bis(trimethylsilyloxy)-5-(trimethylsilyloxymethyl)oxolan-2-yl]-6-oxo-3H-purin-2-yl]carbamate 生成 2-N-(9-fluorenylmethoxycarbonyl)guanosine
  参考文献：
  名称：

  HAGEN, MICHEAL D.;SCALFI-HAPP, CLAUDIA;HAPP, ERWIN;SHLADEK, STANISLAV, 7TH SYMP. CHEM. NUCL. ACID COMPON., BECHYNE CASTLE, AUG. 30TH - SEPT. 5TH+

  摘要：

  DOI：

文献信息

• Four Phosphates at One Blow: Access to Pentaphosphorylated Magic Spot Nucleotides and Their Analysis by Capillary Electrophoresis
  作者：Thomas M. Haas、Danye Qiu、Markus Häner、Larissa Angebauer、Alexander Ripp、Jyoti Singh、Hans-Georg Koch、Claudia Jessen-Trefzer、Henning J. Jessen

  DOI：10.1021/acs.joc.0c00841

  日期：2020.11.20

  The complex phosphorylation pattern of natural and modified pentaphosphorylated magic spot nucleotides is generated in a highly efficient way. A cyclic pyrophosphoryl phosphoramidite (cPyPA) reagent is used to introduce four phosphates on nucleosides regioselectively in a one-flask key transformation. The obtained magic spot nucleotides are used to develop a capillary electrophoresis UV detection method

  天然和修饰的五磷酸化魔点核苷酸的复杂磷酸化模式以高效方式生成。环状焦磷酸基亚磷酰胺（cPyPA）试剂用于在单烧瓶关键转化中向区域性区域选择性地引入四种磷酸。获得的魔点核苷酸用于开发毛细管电泳UV检测方法，可在复杂的细菌提取物中进行核苷酸分配。
• RNA monomers containing 0-acetal levulinyl ester groups and their use in RNA microarrays
  申请人：THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING/MCGILL UNIVERSITY

  公开号：US10287313B2

  公开（公告）日：2019-05-14

  The present invention is directed to RNA monomers comprising O-acetal levulinyl protecting groups at the 2′ and/or the 5′-hydroxy functionalities of the ribose moiety. Said monomers may be incorporated into oligoribonucleotides or RNA polynucleotides. Furthermore, the invention is directed to methods for the synthesis of said RNA monomers, oligoribonucleotides and RNA polynucleotides, as well as methods for their deprotection and methods for the use of said compounds and compositions comprising said compounds. In particular, such compounds and compositions comprising them are used in methods for light-directed synthesis of RNA microarrays.

  本发明涉及在核糖分子的 2′和/或 5′-羟基官能团上含有 O-乙缩醛乙酰基保护基团的 RNA 单体。所述单体可与寡核苷酸或 RNA 多核苷酸结合。此外，本发明还涉及合成所述 RNA 单体、寡核苷酸和 RNA 多核苷酸的方法，以及它们的脱保护方法和使用所述化合物和包含所述化合物的组合物的方法。特别是，这些化合物和包含它们的组合物可用于 RNA 微阵列的光导合成方法。
• Lackey, Jeremy G.; Mitra, Debbie; Somoza, Mark M., Journal of the American Chemical Society, 2009, vol. 131, p. 8496 - 8502
  作者：Lackey, Jeremy G.、Mitra, Debbie、Somoza, Mark M.、Cerrina, Franco、Damha, Masad J.

  DOI：——

  日期：——
• Synthesis and conformational analysis of phosphate-methylated RNA dinucleotides
  作者：Peter J. L. M. Quaedflieg、Arthur P. Van der Heiden、Leo H. Koole、Annie J. J. M. Coenen、Sjoerd Van der Wal、Emmo M. Meijer

  DOI：10.1021/jo00020a028

  日期：1991.9

  Synthesis of RNA dimers having a methyl phosphotriester group as the internucleoside linkage is reported; six pairs of diasteroisomerically pure systems were prepared, i.e, r(CpU) (15), r(ApU) (16), r(CpC) (17), r(ApC) (18), r(CpG) (19), and r(ApG) (20). Compounds 15-20 are stabilized by a 2'-O-methyl group in the 5'-terminal residue. The present systems represent the third class of backbone-modified RNA oligomers, following the 2'-O-methylribonucleotide phosphorothioates and the 2'-O-methylribonucleotide methyl phosphonates. Our synthetic approach comprises the use of 9-fluorenylmethoxycarbonyl (Fmoc) groups for transient protection of the exocyclic NH2 groups of the bases A, C, and G, levulinoyl (Lev) groups for the transient protection of the 2'-and 3'-OH groups of the 3'-terminal residues, methanolic K2CO3 for the simultaneous removal of Fmoc and Lev groups with full preservation of the methyl phosphotriester function, and finally reversed-phase HPLC separation of the S(P) and R(P) diastereoisomers. The availability of the six dimers in diastereoisomerically pure form enabled us to examine the molecular conformations using high-field NMR and circular dichroism (CD) spectroscopy. These studies led to the following conclusions: (i) NMR J-coupling analysis: the central C4'-C5' (gamma) and C5'-O5' (beta) bonds in 15-20 show less preference for the gamma+ and beta-t rotamers, in comparison with their natural analogues, i.e., base stacking is diminished upon introduction of the two methyl groups on O2' and on the phosphate methyl groups on O2' and on the phosphate group; (ii) CD analysis: 15-20 show substantially reduced molecular ellipticities when compared to the natural counterparts, which also reveals that base stacking is reduced; (iii) UV and variable-temperature H-1 NMR measurements: (S(P)- and (R(P))-19 show self-association, via the formation of a right-handed miniduplex with two C-G base pairs ((S(P)-19, T(m) = 9.3-degrees-C, concn = 36.6-mu-M; (R(P))-19, T(m) = 8.7-degrees-C, concn = 48.1-mu-M). The present conformational data on (R(P))- and (S(P))-15-20 are in agreement with literature data on other phosphate-triesterified oligonucleotides, e.g., the trimer d(T(POEt)G(POEt)G) and the tetramer d(T(POEt)T(POEt)C(POEt)A). While the latter systems also showed little base-base stacking, it was established that they readily form a local duplex with a complementary natural RNA sequence. Hence we anticipate that phosphate-methylated 2'-O-methyl-RNA oligomers, longer than the dimer systems described in the present work, will also hybridize easily with complementary natural RNA.
• Aminoacyl derivatives of nucleosides, nucleotides, and polynucleotides. 45. Synthesis of 2'(3')-O-(aminoacyl) trinucleotides incorporating all four common bases
  作者：Michael D. Hagen、Claudia Scalfi-Happ、Erwin Happ、Stanislav Chladek

  DOI：10.1021/jo00256a025

  日期：1988.10