Backbone amide linker strategy for the synthesis of 1,4-triazole-containing cyclic tetra- and pentapeptides

被引:21
作者
Springer, Jasper [1 ]
de Cuba, Kimberly R. [1 ]
Calvet-Vitale, Sandrine [1 ]
Geenevasen, Jan A. J. [1 ]
Hermkens, Pedro H. H. [2 ]
Hiemstra, Henk [1 ]
van Maarseveen, Jan H. [1 ]
机构
[1] Univ Amsterdam, Fac Sci, Vant Hoff Inst Mol Sci, NL-1018 WS Amsterdam, Netherlands
[2] NV Organon, NL-5340 BH Oss, Netherlands
关键词
BAL strategy; cyclic peptides; click chemistry; triazole;
D O I
10.1002/ejoc.200800143
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A backbone amide linker strategy was chosen for the solid-phase synthesis of triazole-containing Cyclic tetra- and pentapeptides. An alkyne-substituted linker derived from 4-hydroxy-2-methoxybenzaldehyde was elongated by using standard "Fmoc-based" solid phase chemistry and terminated by coupling of an azido acid. In solution, the peptides were cyclized by a Cu-1-catalyzed azide-alkyne cycloaddition reaction. The solid-supported synthesized linear peptides had to be cleaved prior to cyclization. As an example of cyclic tetrapeptides, a triazole analog of cyclo-[Pro-Val-Pro-Tyr] (2) was prepared by the solid-phase/solution-phase method. For the cyclic pentapeptides, segetalin B (3) was chosen as a model compound to show the applicability of this method. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
引用
收藏
页码:2592 / 2600
页数:9
相关论文
共 42 条
[1]  
Alsina J, 1999, CHEM-EUR J, V5, P2787, DOI 10.1002/(SICI)1521-3765(19991001)5:10<2787::AID-CHEM2787>3.0.CO
[2]  
2-2
[3]   An alternative method for the preparation of resin-bound secondary amines [J].
Austin, RE ;
Waldraff, CA ;
Al-Obeidi, F .
TETRAHEDRON LETTERS, 2002, 43 (19) :3555-3556
[4]   A solid phase linker strategy for the direct synthesis of EDANS-labelled peptide substrates [J].
Beythien, J ;
White, PD .
TETRAHEDRON LETTERS, 2005, 46 (01) :101-104
[5]   CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].
Bock, VD ;
Hiemstra, H ;
van Maarseveen, JH .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68
[6]   Click chemistry as a route to cyclic tetrapeptide analogues:: Synthesis of cyclo-[Pro-Val-Ψ(triazole)-Pro-Tyr] [J].
Bock, VD ;
Perciaccante, R ;
Jansen, TP ;
Hiemstra, H ;
van Maarseveen, JH .
ORGANIC LETTERS, 2006, 8 (05) :919-922
[7]   1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics [J].
Bock, Victoria D. ;
Speijer, Dave ;
Hiemstra, Henk ;
van Maarseveen, Jan H. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (06) :971-975
[8]   AN EXPEDIENT AND HIGH-YIELDING METHOD FOR THE SOLID-PHASE SYNTHESIS OF DIVERSE 1,4-BENZODIAZEPINE-2,5-DIONES [J].
BOOJAMRA, CG ;
BUROW, KM ;
ELLMAN, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18) :5742-5743
[9]   A backbone linker for BOC-based peptide synthesis and on-resin cyclization: Synthesis of stylostatin 1 [J].
Bourne, GT ;
Meutermans, WDF ;
Alewood, PF ;
McGeary, RP ;
Scanlon, M ;
Watson, AA ;
Smythe, ML .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :3095-3101
[10]   GRAMICIDIN-S - THE SEQUENCE OF THE AMINO-ACID RESIDUES [J].
CONSDEN, R ;
GORDON, AH ;
MARTIN, AJP ;
SYNGE, RLM .
BIOCHEMICAL JOURNAL, 1947, 41 (04) :596-602