Development of a hypusine reagent for peptide synthesis

被引:18
作者
Bergeron, RJ
Ludin, C
Muller, R
Smith, RE
Phanstiel, O
机构
[1] UNIV BERN,INST ORGAN CHEM,CH-3012 BERN,SWITZERLAND
[2] UNIV CENT FLORIDA,DEPT CHEM,ORLANDO,FL 32816
关键词
D O I
10.1021/jo970119z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of a reagent that enables the incorporation of the unusual amino acid (2S,9R)hypusine (Hpu) into peptide sequences is described. The reagent, (2S,SR)-11-[(benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2- [(9-fluorenylmethoxycarbonyl)amino]-9-(tetrahydropyran-2-yloxy)- 7-azaundecanoic acid, is utilized in the synthesis of a hexapeptide containing the primary pentapeptide sequence of the eukaryotic initiation factor eIF-5A, L-Cys-L-Thr-Gly-Hpu-L-His-Gly. The reagent is shown to be effective for both solution phase and Merrifield resin synthesis.
引用
收藏
页码:3285 / 3290
页数:6
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