NOVEL SOLID SUPPORTS FOR THE PREPARATION OF 3'-DERIVATIZED OLIGONUCLEOTIDES - INTRODUCTION OF 3'-ALKYLPHOSPHATE TETHER GROUPS BEARING AMINO, CARBOXY, CARBOXAMIDO, AND MERCAPTO FUNCTIONALITIES

被引：38
作者：
HOVINEN, J [1 ]
GUZAEV, A [1 ]
AZHAYEV, A [1 ]
LONNBERG, H [1 ]
机构：
[1] UNIV TURKU,DEPT CHEM,SF-20500 TURKU,FINLAND
来源：
TETRAHEDRON | 1994年 / 50卷 / 24期
关键词：
D O I：
10.1016/S0040-4020(01)85244-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Syntheses of 5 non-nucleosidic solid supports (1-5) that enable preparation of oligonucleotides bearing a carboxy,-amino,-carboxamido,-or mercaptoalkyl spacer arm at their 3'-terminus are described. They all contain an ester bond of moderate susceptibility toward nucleophiles. Upon the completion of oligonucleotide chain assembly, this bond may be cleaved by a variety of nucleophiles. These release the oligonucleotide from the support and simultaneously introduce the desired functionality. Differences in the reactivity between the supports prepared are discussed.
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页码：7203 / 7218
页数：16
相关论文
共 35 条
[11]  
GAMBER HB, 1993, NUCLEIC ACIDS RES, V21, P145
[12]   SYNTHESIS OF OLIGONUCLEOTIDES CONTAINING A CARBOXYL GROUP AT EITHER THEIR 5' END OR THEIR 3' END AND THEIR SUBSEQUENT DERIVATIZATION BY AN INTERCALATING AGENT [J].
GOTTIKH, M ;
ASSELINE, U ;
THUONG, NT .
TETRAHEDRON LETTERS, 1990, 31 (46) :6657-6660
[13]   PHOTOCHEMICAL CLEAVAGE OF OLIGONUCLEOTIDES FROM SOLID-PHASE SUPPORTS [J].
GREENBERG, MM .
TETRAHEDRON LETTERS, 1993, 34 (02) :251-254
[14]   ANCHOR FOR ONE-STEP RELEASE OF 3'-AMINOOLIGONUCLEOTIDES FROM A SOLID SUPPORT [J].
GRYAZNOV, SM ;
LETSINGER, RL .
TETRAHEDRON LETTERS, 1993, 34 (08) :1261-1264
[15]   A GENERAL-METHOD FOR THE SYNTHESIS OF 3'-SULFHYDRYL AND PHOSPHATE GROUP CONTAINING OLIGONUCLEOTIDES [J].
GUPTA, KC ;
SHARMA, P ;
KUMAR, P ;
SATHYANARAYANA, S .
NUCLEIC ACIDS RESEARCH, 1991, 19 (11) :3019-3025
[16]   A UNIVERSAL SOLID SUPPORT FOR THE SYNTHESIS OF 3'-THIOL GROUP CONTAINING OLIGONUCLEOTIDES [J].
GUPTA, KC ;
SHARMA, P ;
SATHYANARAYANA, S ;
KUMAR, P .
TETRAHEDRON LETTERS, 1990, 31 (17) :2471-2474
[17]  
GUZAEV AP, 1991, NUCLEIC ACIDS RES S, V24, P236
[18]   THE SYNTHESIS OF POLYAMIDE OLIGONUCLEOTIDE CONJUGATE MOLECULES [J].
HARALAMBIDIS, J ;
DUNCAN, L ;
ANGUS, K ;
TREGEAR, GW .
NUCLEIC ACIDS RESEARCH, 1990, 18 (03) :493-499
[19]   3'-MODIFIED ANTISENSE OLIGODEOXYRIBONUCLEOTIDES COMPLEMENTARY TO CAMODULIN MESSENGER-RNA ALTER BEHAVIORAL-RESPONSES IN PARAMECIUM [J].
HINRICHSEN, RD ;
FRAGA, D ;
REED, MW .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (18) :8601-8605
[20]   SYNTHESIS OF 3'-FUNCTIONALIZED OLIGONUCLEOTIDES ON A SINGLE SOLID SUPPORT [J].
HOVINEN, J ;
GUZAEV, A ;
AZHAYEV, A ;
LONNBERG, H .
TETRAHEDRON LETTERS, 1993, 34 (50) :8169-8172
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