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• W2012304070 endingPage "5305" @default.
• W2012304070 startingPage "5298" @default.
• W2012304070 abstract "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." @default.
• W2012304070 created "2016-06-24" @default.
• W2012304070 creator A5008793083 @default.
• W2012304070 creator A5029891406 @default.
• W2012304070 creator A5053911504 @default.
• W2012304070 creator A5062846094 @default.
• W2012304070 date "2008-05-01" @default.
• W2012304070 modified "2023-09-23" @default.
• W2012304070 title "Synthesis of diamino-furostan sapogenins and their use as scaffolds for positioning peptides in a preorganized form" @default.
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