'O-acyl isopeptide method':: racemization-free segment condensation in solid phase peptide synthesis

被引:41
作者
Yoshiya, Taku
Sohma, Youhei
Kimura, Tooru
Hayashia, Yoshio
Kiso, Yoshiaki [1 ]
机构
[1] Kyoto Pharmaceut Univ, Dept Med Chem, Ctr Frontier Res Med Sci, 21st Century COE Program,Yamashina Ku, Kyoto 6078412, Japan
[2] Kyoto Pharmaceut Univ, Dept Chem Phys, 21st Century COE Program, Yamashina Ku, Kyoto 6078412, Japan
基金
日本学术振兴会;
关键词
O-acyl isodipeptide unit; O-acyl isopeptide method; O-N intramolecular acyl migration; racemization-free; segment condensation;
D O I
10.1016/j.tetlet.2006.09.001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We disclosed a novel 'racemization-free segment condensation' based on the 'O-acyl isopeptide method' in which an N-segment including C-terminal O-acyl isopeptide structure with urethane-protected Ser/Thr residue was employed for the segment condensation, suggesting that the use of this method contributes to the effective convergent synthesis of long peptides/proteins. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7905 / 7909
页数:5
相关论文
共 34 条
[1]   Efficient synthesis of peptaibol using a chloroimidazolidium coupling reagent, CIP [J].
Akaji, K ;
Tamai, Y ;
Kiso, Y .
TETRAHEDRON, 1997, 53 (02) :567-584
[2]   Kinetically controlled ligation for the convergent chemical synthesis of proteins [J].
Bang, Duhee ;
Pentelute, Brad L. ;
Kent, Stephen B. H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) :3985-3988
[3]  
Barlos K, 1999, BIOPOLYMERS, V51, P266, DOI 10.1002/(SICI)1097-0282(1999)51:4<266::AID-BIP3>3.0.CO
[4]  
2-U
[5]  
BENZ H, 1994, SYNTHESIS-STUTTGART, P337
[6]   Synthesis of 'difficult' peptide sequences:: application of a depsipeptide technique to the Jung-Redemann 10- and 26-mers and the amyloid peptide Aβ(1-42) [J].
Carpino, LA ;
Krause, E ;
Sferdean, CD ;
Schümann, M ;
Fabian, H ;
Bienert, M ;
Beyermann, M .
TETRAHEDRON LETTERS, 2004, 45 (40) :7519-7523
[7]   Depsipeptide methodology for solid-phase peptide synthesis:: Circumventing side reactions and development of an automated technique via depsidipeptide units [J].
Coin, Irene ;
Doelling, Rudolf ;
Krause, Eberhard ;
Bienert, Michael ;
Beyermann, Michael ;
Sferdean, Calin Dan ;
Carpino, Louis A. .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16) :6171-6177
[8]  
DORNER B, 2005, PEPTIDE SCI 2004, P51
[9]   Convergent solid-phase synthesis of hirudin [J].
Goulas, S ;
Gatos, D ;
Barlos, K .
JOURNAL OF PEPTIDE SCIENCE, 2006, 12 (02) :116-123
[10]   Fragment condensation on solid-phase in the synthesis of an amphiphilic glycopeptide from the homophilic recognition domain of epithelial cadherin 1 [J].
Habermann, J ;
Kunz, H .
TETRAHEDRON LETTERS, 1998, 39 (27) :4797-4800