PEPTIDE-OLIGONUCLEOTIDE HYBRIDS WITH N-ACYLPHOSPHORAMIDATE LINKAGES

被引：17

作者：

ROBLES, J

PEDROSO, E

GRANDAS, A

机构：

[1] Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, 08028 Barcelona

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 15期

关键词：

D O I：

10.1021/jo00120a032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation of a peptide-oligonucleotide hybrid with an N-acylphosphoramidate linkage has been carried out by (i) phosphitylation of the C-terminal carboxamide of a protected peptide by reaction with a chloroalkoxy(dialkylamino)phosphine in the presence of a base, (ii) coupling of the resulting N-acylphosphorodiamidite onto an oligonucleotide-resin followed by oxidation, and (iii) deprotection and cleavage under basic conditions. The synthetic method takes advantage of the unprecedented reaction of primary carboxamides with electrophilic P-III species and takes place under mild conditions which are compatible with the stability of both the peptide and the oligonucleotide components.

引用

页码：4856 / 4861

页数：6

共 29 条

[21] AGROCIN 84 IS A 6-N-PHOSPHORAMIDATE OF AN ADENINE-NUCLEOTIDE ANALOG
ROBERTS, WP
TATE, ME
KERR, A
[J]. NATURE, 1977, 265 (5592) : 379 - 381
[22] SOLID-PHASE SYNTHESIS OF A MODEL NUCLEOPEPTIDE WITH A PHOSPHODIESTER BOND BETWEEN THE 5' END OF A TRINUCLEOTIDE AND A SERINE RESIDUE
ROBLES, J
PEDROSO, E
GRANDAS, A
[J]. TETRAHEDRON LETTERS, 1991, 32 (34) : 4389 - 4392
[23] STEPWISE SOLID-PHASE SYNTHESIS OF THE NUCLEOPEPTIDE PHAC-PHE-VAL-SER(P(3')ACT)-GLY-OH
ROBLES, J
PEDROSO, E
GRANDAS, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) : 2482 - 2486
[24] STEPWISE SOLID-PHASE SYNTHESIS OF NUCLEOPEPTIDE PHAC-SER(P(5')CATCAT)-GLY-ASP-OH FROM ADENOVIRUS-2 NUCLEOPROTEIN
ROBLES, J
PEDROSO, E
GRANDAS, A
[J]. TETRAHEDRON LETTERS, 1994, 35 (25) : 4449 - 4452
[25] ROBLES J, 1994, INT J PEPT PROT RES, V43, P359
[26] ROBLES J, IN PRESS CURRENT TOP
[27] SASSE K, 1964, HOUBENWEYL METHODEN, V12, P849
[28] FAST OLIGONUCLEOTIDE DEPROTECTION PHOSPHORAMIDITE CHEMISTRY FOR DNA-SYNTHESIS
VU, H
MCCOLLUM, C
JACOBSON, K
THEISEN, P
VINAYAK, R
SPIESS, E
ANDRUS, A
[J]. TETRAHEDRON LETTERS, 1990, 31 (50) : 7269 - 7272
[29] REACTION OF N-ACYLPHOSPHORAMIDIC ACID WITH ALCOHOLS
ZIOUDROU, C
[J]. TETRAHEDRON, 1962, 18 (FEB) : 197 - &

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