Glycerol nucleoside triphosphates: Synthesis and polymerase substrate activities

被引:34
作者
Horhota, Allen T. [1 ]
Szostak, Jack W.
McLaughlin, Larry W.
机构
[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
[2] Massachusetts Gen Hosp, Howard Hughes Med Inst, Boston, MA 02114 USA
[3] Massachusetts Gen Hosp, Dept Mol Biol, Boston, MA 02114 USA
关键词
D O I
10.1021/ol062232u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The synthesis of (S)-glycerol nucleoside triphosphates (gNTPs) and the analysis of their substrate activities for enzymatic polymerization is described. NTPs with simplified carbohydrate backbones such as the tNTPs (alpha-L-threose-NTPs) are polymerase substrates and offer the potential to create non-natural aptamer sequences with simplified backbones through enzymatic means. The acyclic (S)-GNA was modeled after the shortened alpha-threofuranosyl backbone. Here we describe the synthesis of (S)-glycerol NTPs and initial enzymatic testing of this further simplified nucleic acid backbone.
引用
收藏
页码:5345 / 5347
页数:3
相关论文
共 17 条
[11]   RAPID AND EFFICIENT SYNTHESIS OF NUCLEOSIDE 5'-O-(1-THIOTRIPHOSPHATES), 5'-TRIPHOSPHATES AND 2',3'-CYCLOPHOSPHOROTHIOATES USING 2-CHLORO-4H-1,3,2-BENZODIOXAPHOSPHORIN-4-ONE [J].
LUDWIG, J ;
ECKSTEIN, F .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (03) :631-635
[12]   Prebiotic chemistry and the origin of the RNA world [J].
Orgel, LE .
CRITICAL REVIEWS IN BIOCHEMISTRY AND MOLECULAR BIOLOGY, 2004, 39 (02) :99-123
[13]   Chemical etiology of nucleic acid structure:: The α-threofuranosyl-(3′→2′) oligonucleotide system [J].
Schöning, KU ;
Scholz, P ;
Guntha, S ;
Wu, X ;
Krishnamurthy, R ;
Eschenmoser, A .
SCIENCE, 2000, 290 (5495) :1347-1351
[14]   The α-L-threofuranosyl-(3′-2′)-oligonucleotide system ('TNA'):: Synthesis and pairing properties [J].
Schöning, KU ;
Scholz, P ;
Wu, XL ;
Guntha, S ;
Delgado, G ;
Krishnamurthy, R ;
Eschenmoser, A .
HELVETICA CHIMICA ACTA, 2002, 85 (12) :4111-4153
[15]   Expanding the structural and functional diversity of RNA:: analog uridine triphosphates as candidates for in vitro selection of nucleic acids [J].
Vaish, NK ;
Fraley, AW ;
Szostak, JW ;
McLaughlin, LW .
NUCLEIC ACIDS RESEARCH, 2000, 28 (17) :3316-3322
[16]   Synthesis of glycol nucleic acids [J].
Zhang, LL ;
Peritz, AE ;
Carroll, PJ ;
Meggers, E .
SYNTHESIS-STUTTGART, 2006, (04) :645-653
[17]   A simple glycol nucleic acid [J].
Zhang, LL ;
Peritz, A ;
Meggers, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (12) :4174-4175