Synthesis of pyridinone ribonucleoside 3'-O-phosphoramidites and their incorporation into oligoribonucleotides

被引：17
|
作者：
MatulicAdamic, J [1 ]
Gonzalez, C [1 ]
Usman, N [1 ]
Beigelman, L [1 ]
机构：
[1] RIBOZYME PHARMACEUT INC,DEPT CHEM & BIOCHEM,BOULDER,CO 80301
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1996年 / 6卷 / 04期
关键词：
D O I：
10.1016/0960-894X(96)00030-3
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Protected pyridin-2- and pyridin-4-one ribonucleosides 3 and 9 were synthesized using a one-pot reaction of silylated bases with 1-O-acetyl-tri-O-benzoyl-beta-D-ribofuranose (2) in the presence of CF(3)SO(3)SiMe(3) The nucleosides were converted in 4 steps into 3'-O-phosphoramidites 7 and 11 which were incorporated into hammerhead ribozyme substrates using solid-phase phosphoramidite chemistry.
引用
收藏
页码：373 / 378
页数：6
相关论文
共 50 条
  • [41] Synthesis and Incorporation of the Phosphoramidite Derivative of 2′-O-Photocaged 3′-S-Thioguanosine into Oligoribonucleotides: Substrate for Probing the Mechanism of RNA Catalysis
    Li, Nan-Sheng
    Tuttle, Nicole
    Staley, Jonathan P.
    Piccirilli, Joseph A.
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (08): : 3647 - 3652
  • [42] SYNTHESIS OF MODIFIED NUCLEOSIDE 3',5'-BISPHOSPHATES AND THEIR INCORPORATION INTO OLIGORIBONUCLEOTIDES WITH T4 RNA LIGASE
    BARRIO, JR
    BARRIO, MDCG
    LEONARD, NJ
    ENGLAND, TE
    UHLENBECK, OC
    BIOCHEMISTRY, 1978, 17 (11) : 2077 - 2081
  • [43] SYNTHESIS OF RIBONUCLEOSIDE 5'-O-HYDROXYMETHANEPHOSPHONATES
    HOLY, A
    HONG, ND
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1971, 36 (01) : 316 - &
  • [44] RIBONUCLEOSIDE CYCLIC 3',5'-PHOSPHORAMIDATES - SYNTHESIS, STEREOCHEMISTRY, AND CONVERSION INTO RIBONUCLEOSIDE CYCLIC 3',5'-PHOSPHOROTHIOATES AND -[O-18]PHOSPHATES
    BARANIAK, J
    STEC, WJ
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (08): : 1645 - 1656
  • [45] Synthesis of 2'-modified N6-methyladenosine phosphoramidites and their incorporation into siRNA
    Rydzik, Anna M.
    Riether, Doris
    Gottschling, Dirk
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2023, 81
  • [46] Synthesis and incorporation of C(5′)-ethynylated uracil-derived phosphoramidites into RNA
    Eppacher, S
    Christen, M
    Vasella, A
    HELVETICA CHIMICA ACTA, 2004, 87 (12) : 3004 - 3020
  • [47] 2'-O-Propargyl Oligoribonucleotides: Synthesis and Hybridisation
    Groetli, M.
    Douglas, M.
    Eritja, R.
    Sproat, B. S.
    Tetrahedron, 54 (22):
  • [48] SYNTHESIS OF TRIAZOL Cn-RIBONUCLEOSIDE PHOSPHORAMIDITES USING β-RIBOFURANOSYL-Cn-ACETYLENES FOR RNA CATALYSIS PROBING
    Yoneyama, Hiroki
    Hikasa, Fumiko
    Fujisue, Daiki
    Usami, Yoshihide
    Zhao, Zheng-yun
    Harusawa, Shinya
    HETEROCYCLES, 2018, 96 (01) : 106 - 126
  • [49] Synthesis of N3-Methyluridine- and 2′-O-Alkyl/2′-Fluoro-N3-Methyluridine-Modified Phosphoramidites and Their Incorporation into DNA and RNA Oligonucleotides
    Sahoo, Avijit
    Gore, Kiran R.
    CURRENT PROTOCOLS, 2024, 4 (10):
  • [50] Novel Method of Synthesis of 5"-Phosphate 2′-O-ribosylribonucleosides and Their 3′- Phosphoramidites
    Chmielewski, Marcin K.
    Markiewicz, Wojciech T.
    MOLECULES, 2013, 18 (12) : 14780 - 14796
12345