Synthesis and enzymatic stability of phosphodiester-linked peptide - Oligonucleotide hybrids

被引:31
作者
Robles, J [1 ]
Maseda, M [1 ]
Beltran, M [1 ]
Concernau, M [1 ]
Pedroso, E [1 ]
Grandas, A [1 ]
机构
[1] UNIV BARCELONA,FAC QUIM,DEPT QUIM ORGAN,E-08028 BARCELONA,SPAIN
关键词
D O I
10.1021/bc970051u
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Nucleopeptides Ac-Tyr(p(3')dACGT)-Ala-Phe-Gly-NH2, Ac-Thr(p(3')dACGT)-Ala-Phe-Gly-OH, Ac-Ser(p(3')dACGT)-Ala-Phe-Gly-OH, and Phac-Hse(p(3')dACGT)-Ala-Phe-Gly-OH, in which the 3'-end of a tetradeoxyribonucleotide is linked by a phosphodiester bond to a hydroxylated amino acid, were synthesized using a stepwise solid-phase methodology to study the influence of the linking amino acid on their stability to 3'-exonucleases. HPLC analysis of the reaction crudes after treatment of each nucleopeptide with snake venom phosphodiesterase showed that the lability of the amino acid-nucleoside linkage increases in the order Thr < Ser < Hse < Tyr.
引用
收藏
页码:785 / 788
页数:4
相关论文
共 23 条
[1]   SYNTHESIS AND ANTIVIRAL ACTIVITY OF PEPTIDE-OLIGONUCLEOTIDE CONJUGATES PREPARED BY USING N-ALPHA-(BROMOACETYL)PEPTIDES [J].
ARAR, K ;
AUBERTIN, AM ;
ROCHE, AC ;
MONSIGNY, M ;
MAYER, R .
BIOCONJUGATE CHEMISTRY, 1995, 6 (05) :573-577
[2]   SOLID-PHASE SYNTHESIS OF A D-PEPTIDE-PHOSPHOROTHIOATE OLIGODEOXYNUCLEOTIDE CONJUGATE FROM 2 ARMS OF A POLYETHYLENE GLYCOL-POLYSTYRENE SUPPORT [J].
BASU, S ;
WICKSTROM, E .
TETRAHEDRON LETTERS, 1995, 36 (28) :4943-4946
[3]  
BELTRAN M, 1997, IN PRESS LETT PEPT S
[4]   SOLID-PHASE SYNTHESIS OF DIRECTLY LINKED PEPTIDE-OLIGODEOXYNUCLEOTIDE HYBRIDS USING STANDARD SYNTHESIS PROTOCOLS [J].
BERGMANN, F ;
BANNWARTH, W .
TETRAHEDRON LETTERS, 1995, 36 (11) :1839-1842
[5]  
BLACKBURN GM, 1996, NUCL ACIDS CHEM BIOL, P101
[6]   IMPROVED BIOLOGICAL-ACTIVITY OF ANTISENSE OLIGONUCLEOTIDES CONJUGATED TO A FUSOGENIC PEPTIDE [J].
BONGARTZ, JP ;
AUBERTIN, AM ;
MILHAUD, PG ;
LEBLEU, B .
NUCLEIC ACIDS RESEARCH, 1994, 22 (22) :4681-4688
[7]   STEPWISE SOLID-PHASE SYNTHESIS OF OLIGONUCLEOTIDE-PEPTIDE HYBRIDS [J].
DELATORRE, BG ;
AVINO, A ;
TARRASON, G ;
PIULATS, J ;
ALBERICIO, F ;
ERITJA, R .
TETRAHEDRON LETTERS, 1994, 35 (17) :2733-2736
[8]   SOLID-PHASE SYNTHESIS OF THE NUCLEOPEPTIDE FRAGMENT H-ASP-SER[PAAAGTAAGCC]-GLU-OH FROM THE NUCLEOPROTEIN OF BACILLUS-SUBTILIS PHAGE PHI-29 [J].
DREEFTROMP, CM ;
VANDERMAAREL, JCM ;
VANDENELST, H ;
VANDERMAREL, GA ;
VANBOOM, JH .
NUCLEIC ACIDS RESEARCH, 1992, 20 (15) :4015-4020
[9]   SYNTHESIS OF DEFINED PEPTIDE-OLIGONUCLEOTIDE HYBRIDS CONTAINING A NUCLEAR TRANSPORT SIGNAL SEQUENCE [J].
ERITJA, R ;
PONS, A ;
ESCARCELLER, M ;
GIRALT, E ;
ALBERICIO, F .
TETRAHEDRON, 1991, 47 (24) :4113-4120
[10]   THE SOLID-PHASE SYNTHESIS OF OLIGONUCLEOTIDES CONTAINING A 3'-PEPTIDE MOIETY [J].
HARALAMBIDIS, J ;
DUNCAN, L ;
TREGEAR, GW .
TETRAHEDRON LETTERS, 1987, 28 (43) :5199-5202