Nucleic Acids with a Six-Membered 'Carbohydrate' Mimic in the Backbone

被引:66
作者
Herdewijn, Piet [1 ]
机构
[1] Rega Inst, Med Chem Lab, B-3000 Louvain, Belgium
关键词
BASE-PAIRING PROPERTIES; ALTRITOL-MODIFIED SIRNAS; ANTIVIRAL ACTIVITY; CONFORMATIONAL-ANALYSIS; BUILDING-BLOCKS; 1,5-ANHYDROHEXITOL NUCLEOTIDES; OLIGONUCLEOTIDE SYNTHESIS; HOMO-DNA; RNASE-H; 2,4-DIDEOXY-BETA-D-ERYTHRO-HEXOPYRANOSYL NUCLEOSIDES;
D O I
10.1002/cbdv.200900185
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Starting from pyranose nucleic acids, several series of modified nucleic acids with a six-membered carbohydrate moiety (mimic) have been synthesized and analyzed over a period of 20 years, and this work is summarized here. The process starts with structural and conformational considerations, followed by synthetic efforts and a structural analysis, and ends up with a biological confirmation of the concept, demonstrating that these modified nucleic acids represent very valuable tools in chemistry and biology.
引用
收藏
页码:1 / 59
页数:59
相关论文
共 111 条
[1]   Synthesis of D-altritol nucleosides with a 3′-O-Tert-butyldimethylsilyl protecting group [J].
Abramov, M ;
Marchand, A ;
Calleja-Marchand, A ;
Herdewijn, P .
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2004, 23 (1-2) :439-455
[2]  
ABRAMOV M, 2007, CURR PROTOC NUCL ACI
[3]   HNA and ANA high-affinity arrays for detections of DNA and RNA single-base mismatches [J].
Abramov, Mikhail ;
Schepers, Guy ;
Van Aerschot, Arthur ;
Van Hummelen, Paul ;
Herdewijn, Piet .
BIOSENSORS & BIOELECTRONICS, 2008, 23 (11) :1728-1732
[4]   Fmoc-protected altritol phosphoramidite building blocks and their application in the synthesis of altritol nucleic acids (ANAs) [J].
Abramov, Mikhail ;
Schepers, Guy ;
Van Aerschot, Arthur ;
Herdewijn, Piet .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (09) :1446-1456
[5]   Synthesis of protected D-altritol nucleosides as building blocks for oligonucleotide synthesis [J].
Allart, B ;
Busson, R ;
Rozenski, J ;
Van Aerschot, A ;
Herdewijn, P .
TETRAHEDRON, 1999, 55 (21) :6527-6546
[6]  
Allart B, 1999, CHEM-EUR J, V5, P2424, DOI 10.1002/(SICI)1521-3765(19990802)5:8<2424::AID-CHEM2424>3.0.CO
[7]  
2-W
[8]   The synthesis of modified D- and L-anhydrohexitol nucleosides [J].
Andersen, MW ;
Daluge, SM ;
Kerremans, L ;
Herdewijn, P .
TETRAHEDRON LETTERS, 1996, 37 (45) :8147-8150
[9]  
Atkins D, 2000, PHARMAZIE, V55, P615
[10]   INCORPORATION OF HEXOSE NUCLEOSIDE ANALOGS INTO OLIGONUCLEOTIDES - SYNTHESIS, BASE-PAIRING PROPERTIES AND ENZYMATIC STABILITY [J].
AUGUSTYNS, K ;
VANDENDRIESSCHE, F ;
VANAERSCHOT, A ;
BUSSON, R ;
URBANKE, C ;
HERDEWIJN, P .
NUCLEIC ACIDS RESEARCH, 1992, 20 (18) :4711-4716