Recent highlights in modified oligonucleotide chemistry

被引:83
作者
Cobb, Alexander J. A. [1 ]
机构
[1] Univ Reading, Sch Pharm, Reading RG6 2AH, Berks, England
关键词
D O I
10.1039/b709797m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of modified nucleic acids has been the subject of much study ever since the structure of DNA was elucidated by Watson and Crick at Cambridge and Wilkins and Franklin at King's College over half a century ago. This review describes recent developments in the synthesis and application of these artificial nucleic acids, predominantly the phosphoramidites which allow for easy inclusion into oligonucleotides, and is divided into three separate sections. Firstly, modi. cations to the base portion will be discussed followed secondly by modi. cations to the sugar portion. Finally, changes in the type of nucleic acid linker will be discussed in the third section. Peptide Nucleic Acids ( PNAs) are not discussed in this review as they represent a separate and large area of nucleic acid mimics.
引用
收藏
页码:3260 / 3275
页数:16
相关论文
共 118 条
[1]   O6-(benzotriazol-1-yl)inosine derivatives:: Easily synthesized, reactive nucleosides [J].
Bae, Suyeal ;
Lakshman, Mahesh K. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (04) :782-789
[2]   Design and synthesis of a chemically cleavable fluorescent nucleotide, 3′-O-allyl-dGTP-allyl-bodipy-FL-510, as a reversible terminator for DNA sequencing by synthesis [J].
Bi, LR ;
Kim, DH ;
Ju, JY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2542-2543
[3]   Synthesis of dinucleotides with 2′-C to phosphate connections by ring-closing metathesis [J].
Borsting, P ;
Christensen, MS ;
Steffansen, SI ;
Nielsen, P .
TETRAHEDRON, 2006, 62 (06) :1139-1149
[4]   Stabilisation of a nucleic acid three-way junction by an oligonucleotide containing a single 2′-C to 3′-O-phosphate butylene linkage prepared by a tandem RCM-hydrogenation method [J].
Borsting, P ;
Nielsen, KE ;
Nielsen, P .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (11) :2183-2190
[5]   Dinucleotides containing two allyl groups by combinations of allyl phosphotriesters, 5-allyl-, 2′-O-allyl- and 2′-arabino-O-allyl uridine derivatives as substrates for ring-closing metathesis [J].
Borsting, P ;
Freitag, M ;
Nielsen, P .
TETRAHEDRON, 2004, 60 (48) :10955-10966
[6]   Tandem ring-closing metathesis and hydrogenation towards cyclic dinucleotides [J].
Borsting, P ;
Nielsen, P .
CHEMICAL COMMUNICATIONS, 2002, (18) :2140-2141
[7]  
Borsting P, 2002, SYNTHESIS-STUTTGART, P797
[8]   Novel antisense and peptide nucleic acid strategies for controlling gene expression [J].
Braasch, DA ;
Corey, DR .
BIOCHEMISTRY, 2002, 41 (14) :4503-4510
[9]   Antisense inhibition of gene expression in cells by oligonucleotides incorporating locked nucleic acids: effect of mRNA target sequence and chimera design [J].
Braasch, DA ;
Liu, YH ;
Corey, DR .
NUCLEIC ACIDS RESEARCH, 2002, 30 (23) :5160-5167
[10]   Locked nucleic acid (LNA): fine-tuning the recognition of DNA and RNA [J].
Braasch, DA ;
Corey, DR .
CHEMISTRY & BIOLOGY, 2001, 8 (01) :1-7