Replacement of Ala by Aib improves structuration and biological stability in thymine-based α-nucleopeptides

被引:8
作者
Geotti-Bianchini, Piero [1 ,2 ]
Moretto, Alessandro [2 ]
Peggion, Cristina [2 ]
Beyrath, Julien [1 ]
Bianco, Alberto [1 ]
Formaggio, Fernando [2 ]
机构
[1] CNRS, Inst Biol Mol & Cellulaire, Lab Immunol & Chim Therapeut, F-67000 Strasbourg, France
[2] Univ Padua, Dept Chem, I-35131 Padua, Italy
关键词
PEPTIDE NUCLEIC-ACIDS; AMINO; DESIGN; BACKBONE; BINDING; DNA;
D O I
10.1039/b920211k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three thymine-based nucleo-heptapeptides, each containing two nucleo-amino acids and zero, one or four Aib residues, respectively, have been synthesized. A single Aib residue is enough to promote the adoption of a helical structure in our nucleopeptides and to increase significantly their resistance towards enzymatic degradation. The insertion of four Aib residues, out of seven residues in the sequence, affords a rigid, 3(10)-helical nucleopeptide that is substantially unaffected by serum enzymes and is not cytotoxic.
引用
收藏
页码:1315 / 1321
页数:7
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