ANTISENSE OLIGONUCLEOTIDES - STEREOCONTROLLED SYNTHESIS OF PHOSPHOROTHIOATE OLIGONUCLEOTIDES

被引:14
|
作者
SUSKA, A [1 ]
GRAJKOWSKI, A [1 ]
WILK, A [1 ]
UZNANSKI, B [1 ]
BLASZCZYK, J [1 ]
WIECZOREK, M [1 ]
STEC, WJ [1 ]
机构
[1] TECH UNIV LODZ,INST TECH BIOCHEM,PL-90924 LODZ,POLAND
关键词
D O I
10.1351/pac199365040707
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new method of oligo(nucleoside phosphorothioate)s (OligoS) synthesis, based on the oligonucleotide chain extention via DBU-catalyzed reaction of 5'-OH-nucleoside(-tide)with5'-DMT-nucleoside-3'-O-(2-thiono- 1.3.2-oxathiaphospholane)s (2) is elaborated. The process of oxathiaphospholane ring opening is shown to be chemo- and stereoselective. The use of separated diastereoisomers of 2 allows the synthesis of OligoS with a predetermined sense of chirality at each internucleotide phosphorothioate function.
引用
收藏
页码:707 / 714
页数:8
相关论文
共 50 条
  • [1] Progress on the Stereocontrolled Synthesis of Phosphorothioate Oligonucleotides
    Cao, Shujie
    Li, Hongjun
    Guan, Wenli
    Ren, Mengtian
    Zhou, Chuanzheng
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2023, 44 (03):
  • [2] Oxathiaphospholane method of the stereocontrolled synthesis of phosphorothioate analogues of oligonucleotides
    Okruszek, A
    RNA BIOCHEMISTRY AND BIOTECHNOLOGY, 1999, 70 : 325 - 334
  • [3] Solid-Phase Synthesis of Boranophosphate/Phosphorothioate/Phosphate Chimeric Oligonucleotides and Their Potential as Antisense Oligonucleotides
    Takahashi, Yuhei
    Sato, Kazuki
    Wada, Takeshi
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (06): : 3895 - 3909
  • [4] IN-VITRO PHARMACOKINETICS OF PHOSPHOROTHIOATE ANTISENSE OLIGONUCLEOTIDES
    CROOKE, RM
    GRAHAM, MJ
    COOKE, ME
    CROOKE, ST
    JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 1995, 275 (01): : 462 - 473
  • [5] MODULATION OF MURINE HEMATOPOIESIS BY ANTISENSE PHOSPHOROTHIOATE OLIGONUCLEOTIDES
    PATINKIN, D
    EHRLICH, G
    ECKSTEIN, F
    SOREQ, H
    EXPERIMENTAL HEMATOLOGY, 1993, 21 (08) : 1023 - 1023
  • [6] Efficient synthesis of antisense phosphorothioate oligonucleotides using a universal solid support
    Kumar, RK
    Guzaev, AP
    Rentel, C
    Ravikumar, VT
    TETRAHEDRON, 2006, 62 (18) : 4528 - 4534
  • [7] RING-OPENING CONDENSATION AS THE BASIS FOR THE STEREOCONTROLLED SYNTHESIS OF PHOSPHOROTHIOATE ANALOGS OF OLIGONUCLEOTIDES
    STEC, WJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 25 - CARB
  • [8] Endocytosis of Phosphorothioate Antisense Oligonucleotides (ASO) by the Stabilin Receptors
    Egger, Andrew
    Keller, Brianna
    Miller, Colton M.
    Harris, Edward N.
    FASEB JOURNAL, 2017, 31
  • [9] Labeling of phosphorothioate antisense oligonucleotides with yttrium-90
    Watanabe, N
    Sawai, H
    Endo, K
    Shinozuka, K
    Ozaki, H
    Tanada, S
    Murata, H
    Sasaki, Y
    NUCLEAR MEDICINE AND BIOLOGY, 1999, 26 (02) : 239 - 243
  • [10] A review of issues in the pharmacokinetics and toxicology of phosphorothioate antisense oligonucleotides
    Levin, AA
    BIOCHIMICA ET BIOPHYSICA ACTA-GENE STRUCTURE AND EXPRESSION, 1999, 1489 (01): : 69 - 84