Synthesis and properties of carbohydrate–phosphate backbone-modified oligonucleotide analogues and nucleic acid mimetics

作者: Tatyana V Abramova , Vladimir N Silnikov

DOI: 10.1070/RC2011V080N05ABEH004188

关键词: Nucleic acid analogueMorpholinoPeptideChemistryPhosphateNucleic acidStereochemistryPhosphonateNucleosideOligonucleotideGeneral chemistry

摘要: Advances in the synthesis of oligo(deoxy)ribonu- cleotide analogues and nucleic acid mimetics made last decade are summarized. Attention is focused on new methods for derivatives with a modified ribose-phosphate backbone (phosphorothioate, borano- phosphate, nucleoside phosphonate derivatives) devoid phosphate group. Among mimetics, conformationally restricted peptide acids, including those bearing negative or positive charge, morpholino oligomers considered. Advan- tages drawbacks main types as regards complexity possibility their application antisense agents reagents hybrid- ization analysis compared. The bibliography includes 282 references references..

参考文章(187)
Hemavathi Challa, Thomas C Bruice, Deoxynucleic guanidine; synthesis and incorporation of purine nucleosides into positively charged DNG oligonucleotides. Bioorganic & Medicinal Chemistry. ,vol. 12, pp. 1475- 1481 ,(2004) , 10.1016/J.BMC.2003.12.043
Fritz Eckstein, Oligonucleotides and analogues : a practical approach IRL Press : Oxford University Press, c1991. ,(1991)
RV Giles, DG Spiller, JA Green, RE Clark, DM Tidd, Optimization of antisense oligodeoxynucleotide structure for targeting bcr-abl mRNA Blood. ,vol. 86, pp. 744- 754 ,(1995) , 10.1182/BLOOD.V86.2.744.BLOODJOURNAL862744
Sudhir Agrawal, Stanley T. Crooke, Antisense Research and Applications ,(1993)
Pravin S. Shirude, Vaijayanti A. Kumar, Krishna N. Ganesh, (2S,5R/2R,5S)-Aminoethylpipecolyl aepip-aegPNA chimera: synthesis and duplex/triplex stability Tetrahedron. ,vol. 60, pp. 9485- 9491 ,(2004) , 10.1016/J.TET.2004.07.080
Koen Robeyns, Piet Herdewijn, Luc Van Meervelt, Structure of the fully modified left-handed cyclohexene nucleic acid sequence GTGTACAC Journal of the American Chemical Society. ,vol. 130, pp. 1979- 1984 ,(2007) , 10.1021/JA077313F
S. V. Kochetkova, A. M. Varizhuk, N. A. Kolganova, E. N. Timofeev, V. L. Florent’ev, [Synthesis of 3'-deoxy-3'-carboxymethylnucleosides, precursors of oligonucleotides with an amide internucleoside bond]. Russian Journal of Bioorganic Chemistry. ,vol. 35, pp. 68- 74 ,(2009) , 10.1134/S1068162009010099