A nonacid degradable linker for solid-phase synthesis

被引:7
作者
Colombo, Aina
De la Figuera, Natalia
Fernandez, Joan Carles
Fernandez-Forner, Dolors
Albericio, Fernando
Forns, Pilar
机构
[1] Almirall Barcelona Sci Pk Unit, E-08028 Barcelona, Spain
[2] Res Ctr, Almirall & Prodesfarma, E-08024 Barcelona, Spain
[3] Univ Barcelona, Inst Res Biomed, Barcelona Sci Pk, E-08028 Barcelona, Spain
[4] Univ Barcelona, Dept Organ Chem, E-08028 Barcelona, Spain
关键词
D O I
10.1021/ol701879s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis and applications of two new nonacid degradable linkers as an alternative to the Wang linker for solid-phase synthesis are described. Resin from linker 2 looks superior to linker 1 in terms of yields for both anchoring of the first building block and cleavage and in terms of higher purity of the final product. Use of linker 2 avoids side reactions associated with the use of Wang resin due to an undesired cleavage during final acid treatment.
引用
收藏
页码:4319 / 4322
页数:4
相关论文
共 50 条
[21]   Novel linker for solid-phase synthesis of dimeric compounds. [J].
Pattarawarapan, M ;
Burgess, K .
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 :U40-U40
[22]   Solid-phase synthesis of peptide esters employing the hydrazide linker [J].
Peters, C ;
Waldmann, H .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (15) :6053-6055
[23]   A Dde-based carboxy linker for solid-phase synthesis [J].
Chhabra, SR ;
Parekh, H ;
Khan, AN ;
Bycroft, BW ;
Kellam, B .
TETRAHEDRON LETTERS, 2001, 42 (11) :2189-2192
[24]   A SILICON-BASED LINKER FOR TRACELESS SOLID-PHASE SYNTHESIS [J].
PLUNKETT, MJ ;
ELLMAN, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :6006-6007
[25]   An oxidation-labile traceless linker for solid-phase synthesis [J].
Stieber, F ;
Grether, U ;
Waldmann, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (08) :1073-1077
[26]   An alkanesulfonamide "safety-catch" linker for solid-phase synthesis [J].
Backes, BJ ;
Ellman, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2322-2330
[27]   A new versatile linker for the solid-phase synthesis of secondary amines [J].
Glatz, H ;
Bannwarth, W .
TETRAHEDRON LETTERS, 2003, 44 (01) :149-152
[28]   A simple oxazolidine linker for solid-phase synthesis of peptide aldehydes [J].
Kang, Wu ;
Wang, Weiguo ;
Zhi, XiaoXia ;
Zhang, Bo ;
Wei, Ping ;
Xu, HongYan .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (02) :1187-1188
[29]   Acetophenone-based linker for solid-phase peptide synthesis [J].
Bui, CT ;
Bray, AM ;
Nguyen, T ;
Ercole, F ;
Rasoul, F ;
Sampson, W ;
Maeji, NJ .
JOURNAL OF PEPTIDE SCIENCE, 2000, 6 (02) :49-56
[30]   Silicon-based linker for traceless solid-phase synthesis [J].
Plunkett, Matthew J. ;
Ellman, Jonathan A. .
Journal of Organic Chemistry, 1995, 60 (19)