4-N-(9-fluorenylmethoxycarbonyl)cytidine | 87424-16-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 4-N-(9-fluorenylmethoxycarbonyl)cytidine
• 英文别名: 9H-fluoren-9-ylmethyl N-[1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]carbamate
• CAS: 87424-16-6
• 化学式: C₂₄H₂₃N₃O₇
• 分子量: 465.463
• InChiKey: MAPUOPVPIROXMX-ZHHKINOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-N-(9-fluorenylmethoxycarbonyl)cytidine 在 ammonium hydroxide 作用下， 以 吡啶 为溶剂， 反应 0.5h， 生成 胞苷
  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：

  阿扎胞苷杂质20 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 4.17h， 生成 4-N-(9-fluorenylmethoxycarbonyl)cytidine
  参考文献：
  名称：

  Aminoacyl derivatives of nucleosides, nucleotides and polynucleotides. 43. New approach to synthesis of 2'(3')-O-aminoacyl oligoribonucleotides

  摘要：

  DOI：

  10.1021/jo00233a015

文献信息

• Heikkilae, Jarmo; Chattopadhyaya, Jyoti, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1983, vol. 37, # 3, p. 263 - 266
  作者：Heikkilae, Jarmo、Chattopadhyaya, Jyoti

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

  DOI：——

  日期：——
• Heikkilae, Jarmo; Chattopadhyaya, Jyoti, Heterocycles, 1984, vol. 21, # 2, p. 542
  作者：Heikkilae, Jarmo、Chattopadhyaya, Jyoti

  DOI：——

  日期：——
• Aminoacyl derivatives of nucleosides, nucleotides and polynucleotides. 43. New approach to synthesis of 2'(3')-O-aminoacyl oligoribonucleotides
  作者：Erwin Happ、Claudia Scalfi-Happ、Stanislav Chladek

  DOI：10.1021/jo00233a015

  日期：1987.11