Effect of molecular sieves in the liquid-phase synthesis of nucleotides via the phosphoramidite method

被引:18
作者
Hayakawa, Y [1 ]
Hirata, A [1 ]
Sugimoto, J [1 ]
Kawai, R [1 ]
Sakakura, A [1 ]
Kataoka, M [1 ]
机构
[1] Nagoya Univ, Bioorgan Chem Lab, Grad Sch Human Informat, Chikusa Ku, Nagoya, Aichi 4648601, Japan
基金
日本学术振兴会;
关键词
nucleotides; molecular sieves; phosphoramidites;
D O I
10.1016/S0040-4020(01)00880-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
It is demonstrated that the reaction of a nucleoside phosphoramidite and a nucleoside aided by a suitable promoter in the presence of molecular sieves 3A or 4A in a liquid phase is efficiently performed by the use of stoichiometric amounts of the reactants to give the desired coupling product in an excellent yield. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8823 / 8826
页数:4
相关论文
共 30 条
[2]   THE SYNTHESIS OF MODIFIED OLIGONUCLEOTIDES BY THE PHOSPHORAMIDITE APPROACH AND THEIR APPLICATIONS [J].
BEAUCAGE, SL ;
IYER, RP .
TETRAHEDRON, 1993, 49 (28) :6123-6194
[3]   The synthesis of allyl- and allyloxycarbonyl-protected RNA posphoramidites. Useful reagents for solid-phase synthesis of RNAs with base-labile modifications. [J].
Bogdan, FM ;
Chow, CS .
TETRAHEDRON LETTERS, 1998, 39 (14) :1897-1900
[4]   SYNTHESIS OF DEOXYDINUCLEOSIDE PHOSPHORODITHIOATES [J].
BRILL, WKD ;
NIELSEN, J ;
CARUTHERS, MH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :3972-3980
[5]   INTERFERON ACTION - 2 DISTINCT PATHWAYS FOR INHIBITION OF PROTEIN-SYNTHESIS BY DOUBLE-STRANDED-RNA [J].
FARRELL, PJ ;
SEN, GC ;
DUBOIS, MF ;
RATNER, L ;
SLATTERY, E ;
LENGYEL, P .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1978, 75 (12) :5893-5897
[6]   Acid/azole complexes as highly effective promoters in the synthesis of DNA and RNA oligomers via the phosphoramidite method [J].
Hayakawa, Y ;
Kawai, R ;
Hirata, A ;
Sugimoto, J ;
Kataoka, M ;
Sakakura, A ;
Hirose, M ;
Noyori, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (34) :8165-8176
[7]   Benzimidazolium triflate as an efficient promoter for nucleotide synthesis via the phosphoramidite method [J].
Hayakawa, Y ;
Kataoka, M ;
Noyori, R .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :7996-7997
[8]   REGIODEFINED SYNTHESIS AND CONFORMATIONAL PROPERTIES OF ADENYLDIYL TRIMERS WITH UNSYMMETRICAL 2'-5' AND 3'-5' INTERNUCLEOTIDE LINKAGES [J].
HAYAKAWA, Y ;
HIROSE, M ;
NOYORI, R .
TETRAHEDRON, 1995, 51 (36) :9899-9916
[9]   THE ALLYLIC PROTECTION METHOD IN SOLID-PHASE OLIGONUCLEOTIDE SYNTHESIS - AN EFFICIENT PREPARATION OF SOLID-ANCHORED DNA OLIGOMERS [J].
HAYAKAWA, Y ;
WAKABAYASHI, S ;
KATO, H ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (05) :1691-1696
[10]   ALLYLOXYCARBONYL GROUP - A VERSATILE BLOCKING GROUP FOR NUCLEOTIDE SYNTHESIS [J].
HAYAKAWA, Y ;
KATO, H ;
UCHIYAMA, M ;
KAJINO, H ;
NOYORI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (12) :2400-2402