Solid-phase synthesis of 1,3-azole-based peptides and peptidomimetics

被引:48
作者
Biron, Eric [1 ]
Chatterjee, Jayanta [1 ]
Kessler, Horst [1 ]
机构
[1] Tech Univ Munich, Dept Chem, Lehrstuhl Organ Chem 2, D-85747 Garching, Germany
关键词
D O I
10.1021/ol0607645
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[graphics] We report highly efficient two-step procedures for the synthesis of 1,3-oxazole-, thiazole-, and imidazole- containing peptides on solid phase from dipeptides composed of C-terminal threonine, serine, cysteine, or diaminopropionic acid by using different cyclodehydration procedures followed or preceded by oxidation. The methods are compatible with Fmoc solid-phase peptide synthesis conditions and with N-Fmoc, N-Boc, N-Cbz, and N-Alloc protecting groups.
引用
收藏
页码:2416 / 2420
页数:4
相关论文
共 61 条
[1]  
Bertram A, 2000, SYNLETT, P1519
[2]  
Bertram A, 2002, HETEROCYCLES, V58, P521
[3]   THE SYNTHESIS OF OPTICALLY-ACTIVE THIAZOLINE AND THIAZOLE DERIVED PEPTIDES FROM N-PROTECTED ALPHA-AMINO-ACIDS [J].
BODEN, CDJ ;
PATTENDEN, G ;
YE, T .
SYNLETT, 1995, (05) :417-419
[4]   Multidrug resistance: A solvable problem? [J].
Borst, P .
ANNALS OF ONCOLOGY, 1999, 10 :162-164
[5]   THE CHIRAL SYNTHESIS OF THIAZOLE AMINO-ACID ENANTIOMERS [J].
BREDENKAMP, MW ;
HOLZAPFEL, CW ;
VANZYL, WJ .
SYNTHETIC COMMUNICATIONS, 1990, 20 (15) :2235-2249
[6]   THERMAL REACTIONS OF ALKYL N-CARBOMETHOXYSULFAMATE ESTERS [J].
BURGESS, EM ;
PENTON, HR ;
TAYLOR, EA .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (01) :26-31
[7]   Initiation factor IF2, thiostrepton and micrococcin prevent the binding of elongation factor G to the Escherichia coli ribosome [J].
Cameron, DM ;
Thompson, J ;
March, PE ;
Dahlberg, AE .
JOURNAL OF MOLECULAR BIOLOGY, 2002, 319 (01) :27-35
[8]   TANTAZOLES - UNUSUAL CYTOTOXIC ALKALOIDS FROM THE BLUE-GREEN-ALGA SCYTONEMA-MIRABILE [J].
CARMELI, S ;
MOORE, RE ;
PATTERSON, GML ;
CORBETT, TH ;
VALERIOTE, FA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8195-8197
[9]   Solid phase combinatorial library of 1,3-azole containing peptides for the discovery of matrix metallo proteinase inhibitors [J].
Christensen, C ;
Schiodt, CB ;
Foged, NT ;
Meldal, M .
QSAR & COMBINATORIAL SCIENCE, 2003, 22 (07) :754-766
[10]   The preparation of polymer bound β-ketoesters and their conversion into an array of oxazoles [J].
Clapham, B ;
Lee, SH ;
Koch, G ;
Zimmermann, J ;
Janda, KD .
TETRAHEDRON LETTERS, 2002, 43 (31) :5407-5410