کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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5228356 | 1383630 | 2008 | 8 صفحه PDF | دانلود رایگان |
The synthesis of peptide-furostane conjugates from natural steroidal sapogenins is reported. The approach comprises the introduction of α-oriented amino groups into spirostanic sapogenins followed by reductive opening of the spiroketal chain, thus producing diamino-furostanic scaffolds suitable for further functionalization. Solid and solution-phase coupling processes were utilized for the incorporation of various α-amino acids and peptides into the furostanic skeletons. The attachment position depends on the steroidal sapogenin originally used, i.e., diosgenin or hecogenin. The resulting furostanic skeletons feature a trans A/B-ring fusion and hold the peptides in axial disposition. This characteristic ensures a preorganized alignment of the peptidic motifs, an important structural feature for future applications in molecular recognition and catalysis. A macrocyclic tripeptide-furostane conjugate was also produced by a combination of peptide coupling, Staudinger ligation, and a cyclization protocol. This work constitutes the first report on the use of furostanic sapogenins as scaffolds for positioning natural amino acids and (cyclo)peptides.
Journal: Tetrahedron - Volume 64, Issue 22, 26 May 2008, Pages 5298-5305