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.
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页码:1347 / 1351
页数:5
相关论文
共 48 条
[1]   Chemical etiology of nucleic acid structure:: Comparing pentopyranosyl-(2′→4′) oligonucleotides with RNA [J].
Beier, M ;
Reck, F ;
Wagner, T ;
Krishnamurthy, R ;
Eschenmoser, A .
SCIENCE, 1999, 283 (5402) :699-703
[2]   WHY PENTOSE AND NOT HEXOSE NUCLEIC-ACIDS .2. PREPARATION OF OLIGONUCLEOTIDES CONTAINING 2',3'-DIDEOXY-BETA-D-GLUCOPYRANOSYL BUILDING-BLOCKS [J].
BOHRINGER, M ;
ROTH, HJ ;
HUNZIKER, J ;
GOBEL, M ;
KRISHNAN, R ;
GIGER, A ;
SCHWEIZER, B ;
SCHREIBER, J ;
LEUMANN, C ;
ESCHENMOSER, A .
HELVETICA CHIMICA ACTA, 1992, 75 (05) :1416-1477
[3]   Pyranosyl-RNA: Chiroselective self-assembly of base sequences by ligative oligomerization of tetranucleotide-2',3'-cyclophosphates (with a commentary concerning the origin of biomolecular homochirality) [J].
Bolli, M ;
Micura, R ;
Eschenmoser, A .
CHEMISTRY & BIOLOGY, 1997, 4 (04) :309-320
[4]   Pyranosyl-RNA: Further observations on replication [J].
Bolli, M ;
Micura, R ;
Pitsch, S ;
Eschenmoser, A .
HELVETICA CHIMICA ACTA, 1997, 80 (06) :1901-1951
[5]  
Breslauer K. J, 1986, THERMODYNAMIC DATA B, P402
[6]  
Cantor CR, 1980, BIOPHYSICAL CHEM 3, P1135
[7]   Hybrids of RNA and arabinonucleic acids (ANA and 2′F-ANA) are substrates of ribonuclease h [J].
Damha, MJ ;
Wilds, CJ ;
Noronha, A ;
Brukner, I ;
Borkow, G ;
Arion, D ;
Parniak, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) :12976-12977
[8]   DESIGN AND SYNTHESIS OF DEOXYNUCLEIC GUANIDINE - A POLYCATION ANALOG OF DNA [J].
DEMPCY, RO ;
ALMARSSON, O ;
BRUICE, TC .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (17) :7864-7868
[9]  
DIEDRICHSEN U, 1993, THESIS ETH ZURICH
[10]  
Egger A, 1999, SYNLETT, P913