Syntheses of [1-15N]-2'-deoxyinosine, [4-15N]-2'-deoxyAICAR, and [1-15N]-2'-deoxyguanosine

被引：0
|
作者：
Catalanotti, B
De Napoli, L
Galeone, A
Mayol, L
Oliviero, G
Piccialli, G
Varra, M
机构：
[1] Univ Naples Federico II, Dipartimento Chim Sostanze Nat, I-80131 Naples, Italy
[2] Univ Naples Federico II, Dipartimento Chim Organ & Biol, I-80134 Naples, Italy
[3] Univ Molise, Fac Sci, I-86170 Isernia, Italy
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 1999卷 / 09期
关键词：
labeled deoxyinosine; labeled deoxyAICAR; labeled deoxyguanosine; purine rearrangement; labeled nucleosides;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A high-yield synthesis of [1-N-15]-2'-deoxyinosine (5), [4-N-15]-2'-deoxy AICAR (7), and [1-N-15]-2'-deoxyguanosine (10) from 2'-deoxyinosine (1) using relatively low expensive (NH3)-N-15 as N-15 source is described. The method exploits 2-C reactivity of 2'-deoxyinosine (1) to obtain its N-15-labelled counterpart, through [1-N-15]-2'-deoxyinosine (5), and successively, [4-N-15]-2'-deoxyAICAR (7). [1-N-15]-2'-Deoxyguanosine (10) can be prepared as well, through an improved cyclization procedure. No protection of sugar hydroxyl groups is required at any stage.
引用
下载
收藏
页码：2235 / 2239
页数：5
相关论文
共 50 条
  • [1] Nitrogen-15-labeled deoxynucleosides. 4. Synthesis of [1-15N]- and [2-15N]-labeled 2 prime -dexyguanosines
    Goswami, Bhaswati
    Jones, Roger A.
    Journal of the American Chemical Society, 1991, 113 (02):
  • [2] Synthesis of [1-15N,2-13C]-labeled difloxacin
    Schmidt, Burkhard
    Schumacher-Buffel, Ramona
    Thiede, Brigitte
    Schaeffer, Andreas
    MONATSHEFTE FUR CHEMIE, 2009, 140 (10): : 1221 - 1227
  • [3] Synthesis of [1-15N,2-13C]-labeled difloxacin
    Burkhard Schmidt
    Ramona Schumacher-Buffel
    Brigitte Thiede
    Andreas Schäffer
    Monatshefte für Chemie - Chemical Monthly, 2009, 140 : 1221 - 1227
  • [4] Magnitudes and orientations of the 15N chemical shift tensor of [1-15N]-2′-deoxyguanosine determined on a polycrystalline sample by two-dimensional solid-state NMR spectroscopy
    Lorigan, GA
    McNamara, R
    Jones, RA
    Opella, SJ
    JOURNAL OF MAGNETIC RESONANCE, 1999, 140 (02) : 315 - 319
  • [5] SYNTHESIS OF [1-N-15]-LABELED 2'-DEOXYINOSINE AND 2'-DEOXYADENOSINE
    DENAPOLI, L
    MESSERE, A
    MONTESARCHIO, D
    PICCIALLI, G
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07): : 2251 - 2253
  • [6] Biosynthesis of [1-15N] l-tryptophan from 15N labeled anthranilic acid by fermentation of Candida utilis mutant
    Liu, Zhanfeng
    Yuan, Qipeng
    Wang, Wenchuan
    AMINO ACIDS, 2009, 36 (01) : 71 - 73
  • [7] Biosynthesis of [1-15N] l-tryptophan from 15N labeled anthranilic acid by fermentation of Candida utilis mutant
    Zhanfeng Liu
    Qipeng Yuan
    Wenchuan Wang
    Amino Acids, 2009, 36 : 71 - 73
  • [8] Use of a C-13 atom to differentiate two N-15-labeled nucleosides. Syntheses of [(NH2)-N-15]-adenosine, [1,NH2-N-15(2)]- and [2-C-13-1,NH2-N-15(2)]-guanosine, and [1,7,NH2-N-15(3)]- and [2-C-13-1,7,NH2-N-15(3)]-2'-deoxyguanosine
    Zhao, H
    Pagano, AR
    Wang, WM
    Shallop, A
    Gaffney, BL
    Jones, RA
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22): : 7832 - 7835
  • [9] [N,1-15N2]-2′-deoxyadenosines
    Terrazas, M
    Ariza, X
    Vilarrasa, J
    ORGANIC LETTERS, 2005, 7 (12) : 2477 - 2479
  • [10] Syntheses of (2′)3′-15N-Amino-(2′)3′-deoxyguanosine and determination of their pKa values by 15N NMR spectroscopy
    Dai, Qing
    Lea, Charles R.
    Lu, Jun
    Piccirilli, Joseph A.
    ORGANIC LETTERS, 2007, 9 (16) : 3057 - 3060
12345