Synthesis of polyamide nucleic acids (PNAs) using a novel Fmoc/Mmt protecting-group combination

被引:36
作者
Breipohl, G
Knolle, J
Langner, D
OMalley, G
Uhlmann, E
机构
[1] Hoechst AG, Central Pharma Research, G 838
关键词
D O I
10.1016/0960-894X(96)00082-0
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The preparation of 9-Fluorenylmethoxycarbonyl(Fmoc) protected building blocks for the synthesis of polyamide nucleic acids (PNAs) is described. Use of 4-Methoxyphenyldiphenylmethyl (Mmt)-protecting groups for the exocyclic amino function of the nucleobases enhances the solubility of the monomers and allows final deprotection by mild acid treatment. The novel synthetic route is exemplified by the synthesis of heptameric and octameric PNAs.
引用
收藏
页码:665 / 670
页数:6
相关论文
共 11 条
[1]  
BREIPOHL G, 1989, INT J PEPT PROT RES, V34, P262
[2]  
BREIPOHL G, Patent No. 0460446
[3]   PYBOP - A NEW PEPTIDE COUPLING REAGENT DEVOID OF TOXIC BY-PRODUCT [J].
COSTE, J ;
LENGUYEN, D ;
CASTRO, B .
TETRAHEDRON LETTERS, 1990, 31 (02) :205-208
[4]   SYNTHESIS OF PEPTIDE NUCLEIC-ACID MONOMERS CONTAINING THE 4 NATURAL NUCLEOBASES - THYMINE, CYTOSINE, ADENINE, AND GUANINE AND THEIR OLIGOMERIZATION [J].
DUEHOLM, KL ;
EGHOLM, M ;
BEHRENS, C ;
CHRISTENSEN, L ;
HANSEN, HF ;
VULPIUS, T ;
PETERSEN, KH ;
BERG, RH ;
NIELSEN, PE ;
BUCHARDT, O .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5767-5773
[5]   PEPTIDE NUCLEIC-ACIDS (PNA) - OLIGONUCLEOTIDE ANALOGS WITH AN ACHIRAL PEPTIDE BACKBONE [J].
EGHOLM, M ;
BUCHARDT, O ;
NIELSEN, PE ;
BERG, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1895-1897
[6]  
EGHOLM M, 1991, SCIENCE, V254, P1497
[7]  
HEIMER EP, 1984, INT J PEPT PROT RES, V23, P203
[8]   FMOC MEDIATED SYNTHESIS OF PEPTIDE NUCLEIC-ACIDS [J].
THOMSON, SA ;
JOSEY, JA ;
CADILLA, R ;
GAUL, MD ;
HASSMAN, CF ;
LUZZIO, MJ ;
PIPE, AJ ;
REED, KL ;
RICCA, DJ ;
WIETHE, RW ;
NOBLE, SA .
TETRAHEDRON, 1995, 51 (22) :6179-6194
[9]   ANTISENSE OLIGONUCLEOTIDES - A NEW THERAPEUTIC PRINCIPLE [J].
UHLMANN, E ;
PEYMAN, A .
CHEMICAL REVIEWS, 1990, 90 (04) :543-584
[10]  
Uhlmann E, 1993, Methods Mol Biol, V20, P355