Azidopeptide nucleic acid. An alternative strategy for solid-phase peptide nucleic acid (PNA) synthesis

被引:39
作者
Debaene, F [1 ]
Winssinger, N [1 ]
机构
[1] Univ Strasbourg, Inst Sci & Ingn Supramol, F-67000 Strasbourg, France
关键词
D O I
10.1021/ol0358408
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical and efficient method for PNA synthesis using an azide group to mask the N-terminus is reported. The deprotection was carried out in 5 min, while couplings were complete within 60 min. The near neutral conditions of the phosphine deprotection combined with the base-free coupling using hydroxybenzotriazole-activated monomers make this approach very mild.
引用
收藏
页码:4445 / 4447
页数:3
相关论文
共 19 条
[1]   ALTERNATIVE PROCEDURES FOR THE MACROLACTAMIZATION OF OMEGA-AZIDO ACIDS [J].
BOSCH, I ;
ROMEA, P ;
URPI, F ;
VILARRASA, J .
TETRAHEDRON LETTERS, 1993, 34 (29) :4671-4674
[2]  
Casale Ralph, 1999, P39
[3]  
Coull J. M., 1996, PCT Int. Appl., Patent No. [9640685, WO 96/40685]
[4]   NEW SYNTHETIC TRICKS - TRIPHENYLPHOSPHINE-MEDIATED AMIDE FORMATION FROM CARBOXYLIC-ACIDS AND AZIDES [J].
GARCIA, J ;
URPI, F ;
VILARRASA, J .
TETRAHEDRON LETTERS, 1984, 25 (42) :4841-4844
[5]   SULFUR-CONTAINING POLYPEPTIDES .I. USE OF N-BENZHYDRYLOXYCARBONYL GROUP AND BENZHYDRYL ESTER [J].
HISKEY, RG ;
ADAMS, JB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (17) :3969-+
[6]   The solid phase synthesis of oligoureas [J].
Kim, JM ;
Bi, YZ ;
Paikoff, SJ ;
Schultz, PG .
TETRAHEDRON LETTERS, 1996, 37 (30) :5305-5308
[7]   Stereocontrolled total synthesis of (-)-ephedradine A (orantine) [J].
Kurosawa, W ;
Kan, T ;
Fukuyama, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (27) :8112-8113
[8]   Synthesis of protein-nucleic acid conjugates by expressed protein ligation [J].
Lovrinovic, M ;
Seidel, R ;
Wacker, R ;
Schroeder, H ;
Seitz, O ;
Engelhard, M ;
Goody, RS ;
Niemeyer, CM .
CHEMICAL COMMUNICATIONS, 2003, (07) :822-823
[9]   Azido acids in a novel method of solid-phase peptide synthesis. [J].
Meldal, M ;
Juliano, MA ;
Jansson, AM .
TETRAHEDRON LETTERS, 1997, 38 (14) :2531-2534
[10]   Peptide nucleic acid. A molecule with two identities [J].
Nielsen, PE .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (07) :624-630