A straightforward synthesis of 5′-peptide oligonucleotide conjugates using Nα-Fmoc-protected amino acids

被引：21

作者：

Ocampo, SM

Albericio, F

Fernández, I

Vilaseca, M

Eritja, R

机构：

[1] CSIC, Inst Mol Biol, E-08034 Barcelona, Spain

[2] Inst Recerca Biomed Barcelona, E-08028 Barcelona, Spain

[3] Univ Barcelona, Fac Quim, Dept Quim Organ, E-08028 Barcelona, Spain

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 20期

关键词：

D O I：

10.1021/ol0514698

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

graph 5 '-Peptide oligonucleotide conjugates were prepared stepwise on a single support using W-Fmoc-protected amino acids and unprotected phosphate groups. The method uses commercially available reagents and is successful with most natural amino acids. The simplicity of the method may encourage researchers to prepare new oligonucleotide-peptide conjugates with novel properties.

引用

收藏

页码：4349 / 4352

页数：4

相关论文

共 29 条

[1] Stepwise solid-phase synthesis of peptide-oligonucleotide phosphorothioate conjugates employing Fmoc peptide chemistry [J].

Antopolsky, M ;

Azhayev, A .

TETRAHEDRON LETTERS, 2000, 41 (47) :9113-9117

[2] Peptide-oligonucleotide phosphorothioate conjugates with membrane translocation and nuclear localization properties [J].

Antopolsky, M ;

Azhayeva, E ;

Tengvall, U ;

Auriola, S ;

Jääskeläinen, I ;

Rönkkö, S ;

Honkakoski, P ;

Urtti, A ;

Lönnberg, H ;

Azhayev, A .

BIOCONJUGATE CHEMISTRY, 1999, 10 (04) :598-606

[3] SYNTHESIS OF OLIGONUCLEOTIDE-PEPTIDE CONJUGATES CONTAINING A KDEL SIGNAL SEQUENCE [J].

ARAR, K ;

MONSIGNY, M ;

MAYER, R .

TETRAHEDRON LETTERS, 1993, 34 (50) :8087-8090

[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] 48000-FOLD ACCELERATION OF HYBRIDIZATION BY CHEMICALLY-MODIFIED OLIGONUCLEOTIDES [J].

COREY, DR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (36) :9373-9374

[6] Solid-phase peptide synthesis using Nα-trityl-amino acids [J].

de la Torre, BG ;

Marcos, MA ;

Eritja, R ;

Albericio, F .

LETTERS IN PEPTIDE SCIENCE, 2001, 8 (06) :331-338

[7] A new solid-phase synthesis of oligonucleotides 3′-conjugated with peptides [J].

De Napoli, L ;

Messere, A ;

Montesarchio, D ;

Piccialli, G ;

Benedetti, E ;

Bucci, E ;

Rossi, F .

BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (02) :395-400

[8] Towards nucleopeptides containing any trifunctional amino acid (II) [J].

Debéthune, L ;

Marchán, V ;

Fàbregas, G ;

Pedroso, E ;

Grandas, A .

TETRAHEDRON, 2002, 58 (34) :6965-6978

[9] 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

[10] ROUTINE PREPARATION OF THIOL OLIGONUCLEOTIDES - APPLICATION TO THE SYNTHESIS OF OLIGONUCLEOTIDE-PEPTIDE HYBRIDS [J].

EDE, NJ ;

TREGEAR, GW ;

HARALAMBIDIS, J .

BIOCONJUGATE CHEMISTRY, 1994, 5 (04) :373-378