STEPWISE REGENERATION AND RECOVERY OF DEOXYRIBONUCLEOSIDE PHOSPHORAMIDITE MONOMERS DURING SOLID-PHASE OLIGONUCLEOTIDE SYNTHESIS

被引:20
作者
SCREMIN, CL
ZHOU, L
SRINIVASACHAR, K
BEAUCAGE, SL
机构
[1] US FDA,CTR BIOL EVALUAT & RES,DIV HEMATOL PROD,BETHESDA,MD 20892
[2] US FDA,CTR DRUG EVALUAT & RES,DIV METAB & ENDOCRINE DRUG PROD,ROCKVILLE,MD 20857
关键词
D O I
10.1021/jo00087a005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Deoxyribonucleoside phosphoramidites 1a-d have been regenerated, in a stepwise manner, during solid-phase oligonucleotide synthesis and have been efficiently reutilized in the solid-phase synthesis of polydeoxyribonucleotides. The activator 1H-tetrazole has also been recovered and recycled.
引用
收藏
页码:1963 / 1966
页数:4
相关论文
共 38 条
[1]   HINDERED DIALKYLAMINO NUCLEOSIDE PHOSPHITE REAGENTS IN THE SYNTHESIS OF 2 DNA 51-MERS [J].
ADAMS, SP ;
KAVKA, KS ;
WYKES, EJ ;
HOLDER, SB ;
GALLUPPI, GR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (03) :661-663
[2]   INHIBITION OF HUMAN IMMUNODEFICIENCY VIRUS IN EARLY INFECTED AND CHRONICALLY INFECTED-CELLS BY ANTISENSE OLIGODEOXYNUCLEOTIDES AND THEIR PHOSPHOROTHIOATE ANALOGS [J].
AGRAWAL, S ;
IKEUCHI, T ;
SUN, D ;
SARIN, PS ;
KONOPKA, A ;
MAIZEL, J ;
ZAMECNIK, PC .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1989, 86 (20) :7790-7794
[3]   DEBENZOYLATION OF N-BENZOYLNUCLEOSIDE DERIVATIVES WITH ETHYLENEDIAMINE-PHENOL [J].
BARNETT, RW ;
LETSINGER, RL .
TETRAHEDRON LETTERS, 1981, 22 (11) :991-994
[4]   ADVANCES IN THE SYNTHESIS OF OLIGONUCLEOTIDES BY THE PHOSPHORAMIDITE APPROACH [J].
BEAUCAGE, SL ;
IYER, RP .
TETRAHEDRON, 1992, 48 (12) :2223-2311
[5]   THE SYNTHESIS OF MODIFIED OLIGONUCLEOTIDES BY THE PHOSPHORAMIDITE APPROACH AND THEIR APPLICATIONS [J].
BEAUCAGE, SL ;
IYER, RP .
TETRAHEDRON, 1993, 49 (28) :6123-6194
[6]   DEOXYNUCLEOSIDE PHOSPHORAMIDITES - A NEW CLASS OF KEY INTERMEDIATES FOR DEOXYPOLYNUCLEOTIDE SYNTHESIS [J].
BEAUCAGE, SL ;
CARUTHERS, MH .
TETRAHEDRON LETTERS, 1981, 22 (20) :1859-1862
[7]   THE REACTION OF TETRAZOLE WITH PHOSPHORAMIDITES AS A MODEL FOR THE NUCLEOTIDE COUPLING STEP [J].
BERNER, S ;
MUHLEGGER, K ;
SELIGER, H .
NUCLEOSIDES & NUCLEOTIDES, 1988, 7 (5-6) :763-767
[8]   STUDIES ON THE ROLE OF TETRAZOLE IN THE ACTIVATION OF PHOSPHORAMIDITES [J].
BERNER, S ;
MUHLEGGER, K ;
SELIGER, H .
NUCLEIC ACIDS RESEARCH, 1989, 17 (03) :853-864
[9]   NUCLEOTIDE CHEMISTRY .38. SYNTHESIS OF 5'-DEOXY-5'-METHYLPHOSPHONATE LINKED THYMIDINE OLIGONUCLEOTIDES [J].
BOHRINGER, MP ;
GRAFF, D ;
CARUTHERS, MH .
TETRAHEDRON LETTERS, 1993, 34 (17) :2723-2726
[10]  
CHIANG MY, 1991, J BIOL CHEM, V266, P18162