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
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
  • [1] New method to prepare peptide - Oligonucleotide conjugates through glyoxylic oxime formation
    Singh, Y
    Defrancq, E
    Dumy, P
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (24): : 8544 - 8546
  • [2] Aldehydic oligonucleotide: A key intermediate for the preparation of oligonucleotide conjugates through oxime bond formation
    Spinelli, N.
    Singh, Y.
    Defrancq, E.
    Dumy, P.
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2007, 26 (8-9): : 883 - 887
  • [3] New strategy for the synthesis of 3′,5′-bifunctionalized oligonucleotide conjugates through sequential formation of chemoselective oxime bonds
    Edupuganti, OP
    Singh, Y
    Defrancq, E
    Dumy, P
    CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (23) : 5988 - 5995
  • [4] The oxime bond formation as a useful tool for the preparation of oligonucleotide conjugates
    Singh, Y
    Edupuganti, OP
    Villien, M
    Defrancq, T
    Dumy, P
    COMPTES RENDUS CHIMIE, 2005, 8 (05) : 789 - 796
  • [5] Efficient preparation of carbohydrate-oligonucleotide conjugates (COCs) using oxime bond formation
    Forget, D
    Renaudet, O
    Defrancq, E
    Dumy, P
    TETRAHEDRON LETTERS, 2001, 42 (44) : 7829 - 7832
  • [6] Chemoselective oxime and thiazolidine bond formation:: A versatile and efficient route to the preparation of 3′-peptide-oligonucleotide conjugates
    Villien, M
    Defrancq, E
    Dumy, P
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2004, 23 (10): : 1657 - 1666
  • [7] Synthesis of oligonucleotide 2′-conjugates via amide bond formation in solution
    Kachalova, AV
    Stetsenko, DA
    Gait, MJ
    Oretskaya, TS
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (03) : 801 - 804
  • [8] Highly efficient synthesis of peptide-oligonucleotide conjugates: Chemoselective oxime and thiazolidine formation
    Forget, D
    Boturyn, D
    Defrancq, E
    Lhomme, J
    Dumy, P
    CHEMISTRY-A EUROPEAN JOURNAL, 2001, 7 (18) : 3976 - 3984
  • [9] A mild and efficient solid-support synthesis of novel oligonucleotide conjugates
    Habus, Ivan
    Xie, Jin
    Iyer, Radhakrishnan P.
    Zhou, Wen-Qiang
    Shen, Ling X.
    Agrawal, Sudhir
    Bioconjugate Chemistry, 9 (02): : 283 - 291
  • [10] A mild and efficient solid-support synthesis of novel oligonucleotide conjugates
    Habus, I
    Xie, J
    Iyer, RP
    Zhou, WQ
    Shen, LX
    Agrawal, S
    BIOCONJUGATE CHEMISTRY, 1998, 9 (02) : 283 - 291