Stability and selectivity of unnatural DNA with five-membered-ring nucleobase analogues

被引：41

作者：

Berger, M ^{[1
]}

Luzzi, SD ^{[1
]}

Henry, AA ^{[1
]}

Romesberg, FE ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 07期

关键词：

D O I：

10.1021/ja012090t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In an effort to develop an orthogonal third base pair for the storage of genetic information, thiophene and furan heterocycles have been examined as nucleobase analogues. The stability of the unnatural bases was evaluated in duplex DNA paired opposite other unnatural bases as well as opposite the natural bases. Several unnatural base pairs are identified that are both reasonably stable and strongly selective against mispairing with native bases. These results expand the potential nucleobase analogues with which the genetic alphabet may be expanded to include five-membered-ring heterocycles.

引用

页码：1222 / 1226

页数：5

共 38 条

[11] RECOGNITION BY VIRAL AND CELLULAR DNA-POLYMERASES OF NUCLEOSIDES BEARING BASES WITH NONSTANDARD HYDROGEN-BONDING PATTERNS
HORLACHER, J
HOTTIGER, M
PODUST, VN
HUBSCHER, U
BENNER, SA
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (14) : 6329 - 6333
[12] HYBRIDIZATION PROPERTIES OF THE 5-METHYL-ISOCYTIDINE ISOGUANOSINE BASE-PAIR IN SYNTHETIC OLIGODEOXYNUCLEOTIDES
HORN, T
CHANG, CA
COLLINS, ML
[J]. NUCLEOSIDES & NUCLEOTIDES, 1995, 14 (3-5): : 1023 - 1026
[13] THE THERMAL-STABILITY OF OLIGONUCLEOTIDE DUPLEXES IS SEQUENCE INDEPENDENT IN TETRAALKYLAMMONIUM SALT-SOLUTIONS - APPLICATION TO IDENTIFYING RECOMBINANT DNA CLONES
JACOBS, KA
RUDERSDORF, R
NEILL, SD
DOUGHERTY, JP
BROWN, EL
FRITSCH, EF
[J]. NUCLEIC ACIDS RESEARCH, 1988, 16 (10) : 4637 - 4650
[14] KORNBERG A, 1992, DNA REPLICATION
[15] Stabilizing effect of 5-nitroindole (universal base) on DNA duplexes immobilized on gel matrix
Kunitsyn, A
Kochetkova, S
Kolganova, N
Tishchenko, E
Gottikh, B
Florentiev, V
[J]. JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 1997, 15 (03) : 597 - 603
[16] Total synthesis of pamamycin-607
Lee, E
Jeong, EJ
Kang, EJ
Sung, LT
Hong, SK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (41) : 10131 - 10132
[17] Expression monitoring by hybridization to high-density oligonucleotide arrays
Lockhart, DJ
Dong, HL
Byrne, MC
Follettie, MT
Gallo, MV
Chee, MS
Mittmann, M
Wang, CW
Kobayashi, M
Horton, H
Brown, EL
[J]. NATURE BIOTECHNOLOGY, 1996, 14 (13) : 1675 - 1680
[18] Recognition of a non-standard base pair by thermostable DNA polymerases
Lutz, MJ
Horlacher, J
Benner, SA
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (10) : 1149 - 1152
[19] Differential discrimination of DNA polymerases for variants of the non-standard nucleobase pair between xanthosine and 2,4-diaminopyrimidine, two components of an expanded genetic alphabet
Lutz, MJ
Held, HA
Hottiger, M
Hubscher, U
Benner, SA
[J]. NUCLEIC ACIDS RESEARCH, 1996, 24 (07) : 1308 - 1313
[20] Hybridization properties of base-modified oligonucleotides within the double and triple helix motif
Luyten, I
Herdewijn, P
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1998, 33 (7-8) : 515 - 576

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