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
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
收藏
页码:1222 / 1226
页数:5
相关论文
共 38 条
  • [31] BETAINE CAN ELIMINATE THE BASE PAIR COMPOSITION DEPENDENCE OF DNA MELTING
    REES, WA
    YAGER, TD
    KORTE, J
    VONHIPPEL, PH
    [J]. BIOCHEMISTRY, 1993, 32 (01) : 137 - 144
  • [32] Beyond guanine quartets: cation-induced formation of homogenous and chimeric DNA tetraplexes incorporating iso-guanine and guanine
    Roberts, C
    Chaput, JC
    Switzer, C
    [J]. CHEMISTRY & BIOLOGY, 1997, 4 (12): : 899 - 908
  • [33] Theoretical and experimental study of isoguanine and isocytosine: Base pairing in an expanded genetic system
    Roberts, C
    Bandaru, R
    Switzer, C
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (20) : 4640 - 4649
  • [34] 2′-deoxyisoguanosine adopts more than one tautomer to form base pairs with thymidine observed by high-resolution crystal structure analysis
    Robinson, H
    Gao, YG
    Bauer, C
    Roberts, C
    Switzer, C
    Wang, AHJ
    [J]. BIOCHEMISTRY, 1998, 37 (31) : 10897 - 10905
  • [35] SCHWEITZER BA, 1995, J AM CHEM SOC, V117, P1863, DOI 10.1021/ja00112a001
  • [36] Efforts toward expansion of the genetic alphabet: Optimization of interbase hydrophobic interactions
    Wu, YQ
    Ogawa, AK
    Berger, M
    McMinn, DL
    Schultz, PG
    Romesberg, FE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (32) : 7621 - 7632
  • [37] YOKOYAMA M, 1995, SYNTHESIS-STUTTGART, P638
  • [38] YOKOYAMA M, 1993, SYNTHESIS-STUTTGART, P517