Chemical etiology of nucleic acid structure:: The α-threofuranosyl-(3′→2′) oligonucleotide system

被引:453
作者
Schöning, KU
Scholz, P
Guntha, S
Wu, X
Krishnamurthy, R
Eschenmoser, A
机构
[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[2] Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
关键词
D O I
10.1126/science.290.5495.1347
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
TNAs [(L)-alpha -threofuranosyl oligonucleotides] containing vicinally connected (3'-->2') phosphodiester bridges undergo informational base pairing in antiparallel strand orientation and are capable of cross-pairing with RNA and DNA. Being derived from a sugar containing only four carbons, TNA is structurally the simplest of all potentially natural oligonucleotide-type nucleic acid alternatives studied thus far. This, along with the base-pairing properties of TNA, warrants close scrutiny of the system in the context of the problem of RNA's origin.
引用
收藏
页码:1347 / 1351
页数:5
相关论文
共 48 条
[11]   WHY PENTOSE AND NOT HEXOSE NUCLEIC-ACIDS .1. INTRODUCTION TO THE PROBLEM, CONFORMATIONAL-ANALYSIS OF OLIGONUCLEOTIDE SINGLE STRANDS CONTAINING 2',3'-DIDEOXYGLUCOPYRANOSYL BUILDING-BLOCKS (HOMO-DNA), AND REFLECTIONS ON THE CONFORMATION OF A-DNA AND B-DNA [J].
ESCHENMOSER, A ;
DOBLER, M .
HELVETICA CHIMICA ACTA, 1992, 75 (01) :218-259
[12]  
Eschenmoser A, 1996, NATO ADV SCI INST SE, V320, P293
[13]   Chemical etiology of nucleic acid structure [J].
Eschenmoser, A .
SCIENCE, 1999, 284 (5423) :2118-2124
[14]  
FISCHER RW, 1992, THESIS ETH ZURICH
[15]   α-helical peptide nucleic acids (αPNAs):: A new paradigm for DNA-binding molecules [J].
Garner, P ;
Dey, S ;
Huang, YM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (10) :2405-2406
[16]   l-Threonic acid-3-methyl ether and l-threonic acid-2, 3-dimethyl ether [J].
Gatzi, K ;
Reichstein, T .
HELVETICA CHIMICA ACTA, 1938, 21 :195-205
[17]   Why pentose- and not hexose-nucleic acids? Purine-purine pairing in homo-DNA: Guanine, isoguanine, 2,6-diaminopurine, and xanthine [J].
Groebke, K ;
Hunziker, J ;
Fraser, W ;
Peng, L ;
Diederichsen, U ;
Zimmermann, K ;
Holzner, A ;
Leumann, C ;
Eschenmoser, A .
HELVETICA CHIMICA ACTA, 1998, 81 (03) :375-474
[18]  
GROEBKE K, 1993, THESIS ETH ZURICH
[19]   OLIGONUCLEOTIDE N3'-]P5' PHOSPHORAMIDATES [J].
GRYAZNOV, SM ;
LLOYD, DH ;
CHEN, JK ;
SCHULZ, RG ;
DEDIONISIO, LA ;
RATMEYER, L ;
WILSON, WD .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (13) :5798-5802
[20]  
HELG AG, 1994, THESIS ETH ZURICH