SYNTHESIS OF A CARBOXAMIDE LINKED T-ASTERISK-T DIMER AND ITS INCORPORATION IN OLIGONUCLEOTIDES

被引：25

作者：

CHUR, A

HOLST, B

DAHL, O

VALENTINHANSEN, P

PEDERSEN, EB

机构：

[1] ODENSE UNIV,DEPT CHEM,CAMPUSVEJ 55,DK-5230 ODENSE,DENMARK

[2] ODENSE UNIV,DEPT MOLEC BIOL,DK-5230 ODENSE,DENMARK

[3] UNIV COPENHAGEN,H C ORSTED INST,DEPT CHEM,DK-2100 COPENHAGEN,DENMARK

来源：

NUCLEIC ACIDS RESEARCH | 1993年 / 21卷 / 22期

关键词：

D O I：

10.1093/nar/21.22.5179

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The condensation of 5'-O-protected 3'-O-(2-amino-ethyl)thymidine with 1,2-dideoxy-1-thyminyl-beta-D-erythro-pentofuranuronic acid gives a T*T dimer with * representing a 3'-OCH2CH2NHC(O)-4' linkage connecting the two pentofuranosyl moieties. The incorporation of this dimer in oligonucleotide sequences show only moderately lowered T(m) values when hybridized with a complementary DNA relative to the unmodified DNA duplex. Consistently, no looped-out or bubble-type structure could be detected in DNA duplexes with an internal T*T module. Moreover, the 5-atom carboxamide linker causes complete stop on DNA polymerization and on exonuclease III degradation.

引用

收藏

页码：5179 / 5183

页数：5

相关论文

共 24 条

[1] PHARMACOKINETICS, BIODISTRIBUTION, AND STABILITY OF OLIGODEOXYNUCLEOTIDE PHOSPHOROTHIOATES IN MICE [J].

AGRAWAL, S ;

TEMSAMANI, J ;

TANG, JY .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (17) :7595-7599

[2] SOLID-PHASE SYNTHESIS OF OLIGODEOXYRIBONUCLEOSIDE PHOSPHORODITHIOATES FROM THIOPHOSPHORAMIDITES [J].

BJERGARDE, K ;

DAHL, O .

NUCLEIC ACIDS RESEARCH, 1991, 19 (21) :5843-5850

[3] ACTION OF SINGLE-STRAND SPECIFIC NUCLEASES ON MODEL DNA HETERODUPLEXES OF DEFINED SIZE AND SEQUENCE [J].

DODGSON, JB ;

WELLS, RD .

BIOCHEMISTRY, 1977, 16 (11) :2374-2379

[4] NITROSOUREIDO NUCLEOSIDES AS POTENTIAL INHIBITORS OF NUCLEOTIDE BIOSYNTHESIS [J].

ELLIOTT, RD ;

THOMAS, HJ ;

SHADDIX, SC ;

ADAMSON, DJ ;

BROCKMAN, RW ;

RIORDAN, JM ;

MONTGOMERY, JA .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (01) :250-254

[5]

GAIT MJ, 1974, J CHEM SOC PERK T 1, P1684, DOI 10.1039/p19740001684

[6] SYNTHETIC ANALOGS OF POLYNUCLEOTIDES .15. SYNTHESIS AND PROPERTIES OF POLY(5'-AMINO-3'-O-CARBOXYMETHYL-2',5'-DIDEOXY-ERYTHRO-PENTONUCLEOSIDES) CONTAINING 3'(O)-]5'(C) ACETAMIDATE LINKAGES [J].

GAIT, MJ ;

JONES, AS ;

JONES, MD ;

SHEPHERD, MJ ;

WALKER, RT .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (06) :1389-1394

[7] NUCLEOTIDES .44. THYMIDINE-5' PYROPHOSPHATE AND TRIPHOSPHATE [J].

GRIFFIN, BE ;

TODD, A .

JOURNAL OF THE CHEMICAL SOCIETY, 1958, (APR) :1389-1393

[8] SYNTHESIS AND HYBRIDIZATION PROPERTIES OF AMIDE-LINKED THYMIDINE DIMERS INCORPORATED INTO OLIGODEOXYNUCLEOTIDES [J].

IDZIAK, I ;

JUST, G ;

DAMHA, MJ ;

GIANNARIS, PA .

TETRAHEDRON LETTERS, 1993, 34 (34) :5417-5420

[9] DUPLEX STABILITIES OF PHOSPHOROTHIOATE, METHYLPHOSPHONATE, AND RNA ANALOGS OF 2 DNA 14-MERS [J].

KIBLERHERZOG, L ;

ZON, G ;

UZNANSKI, B ;

WHITTIER, G ;

WILSON, WD .

NUCLEIC ACIDS RESEARCH, 1991, 19 (11) :2979-2986

[10] REGULATION OF VIRAL EXPRESSION OF HUMAN IMMUNODEFICIENCY VIRUS INVITRO BY AN ANTISENSE PHOSPHOROTHIOATE OLIGODEOXYNUCLEOTIDE AGAINST REV (ART TRS) IN CHRONICALLY INFECTED-CELLS [J].

MATSUKURA, M ;

ZON, G ;

SHINOZUKA, K ;

ROBERTGUROFF, M ;

SHIMADA, T ;

STEIN, CA ;

MITSUYA, H ;

WONGSTAAL, F ;

COHEN, JS ;

BRODER, S .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1989, 86 (11) :4244-4248