Efficient guanidination of the phosphate linkage towards cationic phosphoramidate oligonucleotides

被引：20

作者：

Michel, T ^{[1
]}

Debart, F ^{[1
]}

Vasseur, JJ ^{[1
]}

机构：

[1] Univ Montpellier 2, Lab Chim Organ Biomol Synth, CNRS, UMR 5625,UM 2,CC 008, F-34095 Montpellier 05, France

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 35期

关键词：

D O I：

10.1016/S0040-4039(03)01694-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient postsynthesis method of guanidination of oligonucleotides was employed to introduce several guanidinium groups into internucleotide phosphoramidate linkages. The amino functions of aminobutylphosphoramidate links were converted to guanidine butylphosphoramidates using a solution of O-methylisourea hemisulfate in aqueous ammonia, in a short reaction time. The synthesis of various fully guanidylated oligonucleotides was successfully performed to provide a new class of cationic phosphoramidate oligonucleotides. (C) 2003 Published by Elsevier Ltd.

引用

收藏

页码：6579 / 6582

页数：4

相关论文

共 32 条

[1] SITE-SPECIFIC FUNCTIONALIZATION OF OLIGODEOXYNUCLEOTIDES FOR NONRADIOACTIVE LABELING [J].

AGRAWAL, S ;

TANG, JY .

TETRAHEDRON LETTERS, 1990, 31 (11) :1543-1546

[2] Synthesis, biophysical properties, and nuclease resistance properties of mired backbone oligodeoxynucleotides containing cationic internucleoside guanidinium linkages: Deoxynucleic guanidine/DNA chimeras [J].

Barawkar, DA ;

Bruice, TC .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1998, 95 (19) :11047-11052

[3]

Beardsley RL, 2000, RAPID COMMUN MASS SP, V14, P2147, DOI 10.1002/1097-0231(20001215)14:23<2147::AID-RCM145>3.0.CO

[4]

2-M

[5] Optimization of guanidination procedures for MALDI mass mapping [J].

Beardsley, RL ;

Reilly, JP .

ANALYTICAL CHEMISTRY, 2002, 74 (08) :1884-1890

[6] TOTAL SYNTHESIS OF (+/-)-15-DEOXYSPERGUALIN [J].

BERGERON, RJ ;

MCMANIS, JS .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (09) :1700-1703

[7] 1H-PYRAZOLE-1-CARBOXAMIDINE HYDROCHLORIDE - AN ATTRACTIVE REAGENT FOR GUANYLATION OF AMINES AND ITS APPLICATION TO PEPTIDE-SYNTHESIS [J].

BERNATOWICZ, MS ;

WU, YL ;

MATSUEDA, GR .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2497-2502

[8] 5-(1-propargylamino)-2′-deoxyuridine (UP):: a novel thymidine analogue for generating DNA triplexes with increased stability [J].

Bijapur, J ;

Keppler, MD ;

Bergqvist, S ;

Brown, T ;

Fox, KR .

NUCLEIC ACIDS RESEARCH, 1999, 27 (08) :1802-1809

[9] C-terminal sequence analysis of peptides and proteins using carboxypeptidases and mass spectrometry after derivatization of Lys and Cys residues [J].

Bonetto, V ;

Bergman, AC ;

Jornvall, H ;

Sillard, R .

ANALYTICAL CHEMISTRY, 1997, 69 (07) :1315-1319

[10] STRUCTURE ACTIVITY RELATIONSHIPS OF NOVEL VASOPRESSIN ANTAGONISTS CONTAINING C-TERMINAL DIAMINOALKANES AND (AMINOALKYL)GUANIDINES [J].

CALLAHAN, JF ;

ASHTONSHUE, D ;

BRYAN, HG ;

BRYAN, WM ;

HECKMAN, GD ;

KINTER, LB ;

MCDONALD, JE ;

MOORE, ML ;

SCHMIDT, DB ;

SILVESTRI, JS ;

STASSEN, FL ;

SULAT, L ;

YIM, NCF ;

HUFFMAN, WF .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (02) :391-396

← 1 2 3 4 →