Shortcut Access to Peptidosteroid Conjugates Building Blocks for Solid-Phase Bile Acid Scaffold Decoration by Convergent Ligation 英文参考文献.docVIP

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Shortcut Access to Peptidosteroid Conjugates Building Blocks for Solid-Phase Bile Acid Scaffold Decoration by Convergent Ligation 英文参考文献.doc

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Shortcut Access to Peptidosteroid Conjugates Building Blocks for Solid-Phase Bile Acid Scaffold Decoration by Convergent Ligation 英文参考文献

Molecules 2011, 16, 10168-10186; doi:10.3390/molecules161210168 OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Shortcut Access to Peptidosteroid Conjugates: Building Blocks for Solid-Phase Bile Acid Scaffold Decoration by Convergent Ligation Dieter Verzele, Sara Figaroli and Annemieke Madder * Laboratory for Organic and Biomimetic Chemistry, Department of Organic Chemistry, Faculty of Sciences, Ghent University, B-9000 Ghent, Belgium * Author to whom correspondence should be addressed; E-Mail: annemieke.madder@ugent.be; Tel.: +32-9-264-4472; Fax: +32-9-264-4998. Received: 10 November 2011 / Accepted: 30 November 2011 / Published: 7 December 2011 Abstract: We present three versatile solid-supported scaffold building blocks based on the (deoxy)cholic acid framework and decorated with handles for further derivatization by modern ligation techniques such as click chemistry, Staudinger ligation or native chemical ligation. Straightforward procedures are presented for the synthesis and analysis of the steroid constructs. These building blocks offer a new, facile and shorter access route to bile acid-peptide conjugates on solid-phase with emphasis on heterodipodal conjugates with defined spatial arrangements. As such, we provide versatile new synthons to the toolbox for bile acid decoration. Keywords: bile acids; solid-phase synthesis; scaffold decoration; peptidosteroids; convergent ligation 1. Introduction Among the variety of molecular scaffolds employed in supramolecular chemistry [1–3], steroids in general, and bile acids in particular, have received a great deal of attention over the last decades [4–8]. The interest in these latter natural products is explained by their unique combination of rigidity and chirality, high availability, biocompatibility, and the various functionalization patterns that can be modified in a tunable manner. Distributed around a tetracyclic framework as shown in Figure 1, the well