Shortcut Access to Peptidosteroid Conjugates: Building Blocks for Solid-Phase Bile Acid Scaffold Decoration by Convergent Ligation

doi:10.3390/molecules161210168

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Molecules 2011, 16(12), 10168-10186; doi:10.3390/molecules161210168

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.

Received: 10 November 2011 / Accepted: 30 November 2011 / Published: 7 December 2011

(This article belongs to the Special Issue Steroids)

Download PDF Full-Text [635 KB, uploaded 19 December 2011 12:21 CET]

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

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Cite This Article

MDPI and ACS Style

Verzele, D.; Figaroli, S.; Madder, A. Shortcut Access to Peptidosteroid Conjugates: Building Blocks for Solid-Phase Bile Acid Scaffold Decoration by Convergent Ligation. Molecules 2011, 16, 10168-10186.

AMA Style

Verzele D, Figaroli S, Madder A. Shortcut Access to Peptidosteroid Conjugates: Building Blocks for Solid-Phase Bile Acid Scaffold Decoration by Convergent Ligation. Molecules. 2011; 16(12):10168-10186.

Chicago/Turabian Style

Verzele, Dieter; Figaroli, Sara; Madder, Annemieke. 2011. "Shortcut Access to Peptidosteroid Conjugates: Building Blocks for Solid-Phase Bile Acid Scaffold Decoration by Convergent Ligation." Molecules 16, no. 12: 10168-10186.

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