New solid support for the synthesis of 3′-oligonucleotide conjugates through glyoxylic oxime bond formation

被引：13
|
作者：
Spinelli, Nicolas [1 ]
Edupuganti, Om Prakash [1 ]
Defrancq, Eric [1 ]
Dumy, Pascal [1 ]
机构：
[1] Univ Grenoble 1, Dept Chim Mol, UMR 5250, CNRS,ICMG FR2607, F-38041 Grenoble 9, France
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 02期
关键词：
D O I：
10.1021/ol062607b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel solid support 1 was synthesized to incorporate glyoxylic aldehyde functionality at the oligonucleotide 3'-terminus. 6-mer and 11-mer oligonucleotide sequences containing 3'-glyoxylic aldehyde functionality were prepared by using this support. These modified oligonucleotides were coupled to reporters containing an aminooxy group to prepare oligonucleotide 3'-conjugates through glyoxylic oxime bond formation. The hydrolytic stability of a glyoxylic oxime linkage was also investigated.
引用
收藏
页码：219 / 222
页数：4
相关论文
共 50 条
  • [41] A SELECTIVELY DETACHABLE LINKAGE UNIT BETWEEN 3'-TERMINUS AND SOLID SUPPORT FOR OLIGONUCLEOTIDE SYNTHESIS
    BEAUCAGE, SL
    ANDRUS, A
    FEDERATION PROCEEDINGS, 1986, 45 (06) : 1515 - 1515
  • [42] Synthesis of phosphorothioate oligonucleotide-peptide conjugates by solid phase fragment condensation
    Diala, Irmina
    Osada, Akira
    Maruoka, Shinji
    Imanisi, Takashi
    Murao, Satoshi
    Ato, Taishi
    Ohba, Hideki
    Fujii, Masayuki
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (23) : 6576 - 6578
  • [43] A CONVENIENT SUPPORT FOR THE SYNTHESIS OF OLIGONUCLEOTIDE 3'-PHOSPHATES
    EFIMOV, VA
    KALINKINA, AL
    CHAKHMAKHCHEVA, OG
    BIOORGANICHESKAYA KHIMIYA, 1995, 21 (08): : 612 - 616
  • [44] Synthesis of RGDF-containing cystine peptides by disulfide bond formation on a solid support
    Yamamoto, Y
    Sofuku, S
    JOURNAL OF CHEMICAL RESEARCH-S, 1996, (12): : 520 - 521
  • [45] A conformationally preorganized universal solid support for efficient oligonucleotide synthesis
    Guzaev, AP
    Manoharan, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) : 2380 - 2381
  • [46] Simple Solid-Phase Synthesis and Biological Properties of Carbohydrate- Oligonucleotide Conjugates Modified at the 3′-Terminus
    Ikeda, Yutaka
    Kubota, Daisuke
    Nagasaki, Yukio
    BIOCONJUGATE CHEMISTRY, 2010, 21 (09) : 1685 - 1690
  • [47] An efficient and versatile synthesis of BisPNA-peptide conjugates based on chemoselective oxime formation
    Neuner, P
    Gallo, P
    Orsatti, L
    Fontana, L
    Monaci, P
    BIOCONJUGATE CHEMISTRY, 2003, 14 (02) : 276 - 281
  • [48] Synthesis of peptides and macromolecular conjugates while adsorbed to a solid support
    Dawson, Philip E.
    JOURNAL OF PEPTIDE SCIENCE, 2024, 30
  • [49] Synthesis of Oligonucleotide Conjugates and Phosphorylated Nucleotide Analogues: An Improvement to a Solid Phase Synthetic Approach
    Romanucci, Valeria
    Zarrelli, Armando
    De Napoli, Lorenzo
    Di Marino, Cinzia
    Di Fabio, Giovanni
    JOURNAL OF CHEMISTRY, 2013, 2013
  • [50] A convenient solid-phase method for the synthesis of novel oligonucleotide-folate conjugates
    Kazanova, Eugenia V.
    Zubin, Eugeny M.
    Kachalova, Anna V.
    Volkov, Eugeny M.
    Oretskaya, Tatiana S.
    Stetsenko, Dmitry A.
    Gottikh, Marina B.
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2007, 26 (10-12) : 1273 - 1276
12345