A new method for the preparation of modified oligonucleotides

被引：15

作者：

Gorchs, O ^{[1
]}

Hernández, M ^{[1
]}

Garriga, L ^{[1
]}

Pedroso, E ^{[1
]}

Grandas, A ^{[1
]}

Farràs, J ^{[1
]}

机构：

[1] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Spain

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 11期

关键词：

D O I：

10.1021/ol025643t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] N-Nitrothymidine can be transformed into a phosphoramidite building block suitable for oligonucleotide synthesis using the standard phosphite triester solid-phase approach. The N-nitrothymidine residues remain stable during the elongation cycles and react smoothly with primary amines, furnishing oligonucleotides containing N3-modified thymidines. A number of N3-substituted oligonucleotides have been prepared using this methodology, some of them incorporating aminoalkyl or hydroxyalkyl groups.

引用

页码：1827 / 1830

页数：4

共 21 条

[1] A chemical method for site-specific modification of RNA: The convertible nucleoside approach
Allerson, CR
Chen, SL
Verdine, GL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (32) : 7423 - 7433
[2] ARIZA X, 1994, ANGEW CHEM INT EDIT, V33, P2454
[3] High-yielding preparation of [3-15N]cytidine, [4-15NH2]cytidine, and [3-15N,4,15NH2]cytidine
Ariza, X
Vilarrasa, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (09) : 2827 - 2829
[4] N-nitration, N-15-labeling, and N-to-N linking of hydroxyl-silylated pyrimidine nucleosides
Ariza, X
Farras, J
Serra, C
Vilarrasa, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) : 1547 - 1549
[5] A NEW ROUTE TO N-15-LABELED, N-ALKYL, AND N-AMINO NUCLEOSIDES VIA N-NITRATION OF URIDINES AND INOSINES
ARIZA, X
BOU, V
VILARRASA, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (13) : 3665 - 3673
[6] Banuls V, 2001, EUR J ORG CHEM, V2001, P4693, DOI 10.1002/1099-0690(200112)2001:24<4693::AID-EJOC4693>3.0.CO
[7] 2-J
[8] Eckstein F., 1991, OLIGONUCLEOTIDES ANA
[9] Selective base-pair destabilization enhances binding of a DNA methyltransferase
Erlanson, DA
Wolfe, SA
Chen, L
Verdine, GL
[J]. TETRAHEDRON, 1997, 53 (35) : 12041 - 12056
[10] Nucleosides and nucleotides .160. Synthesis of oligodeoxyribonucleotides containing 5-(N-aminoalkyl)carbamoyl-2'-deoxyuridin by a new postsynthetic modification method and their thermal stability and nuclease-resistance properties
Haginoya, N
Ono, A
Nomura, Y
Ueno, Y
Matsuda, A
[J]. BIOCONJUGATE CHEMISTRY, 1997, 8 (03) : 271 - 280

← 1 2 3 →