Solid phase total synthesis of the 3-amino-6-hydroxy-2-piperidone (Ahp) cyclodepsipeptide and protease inhibitor Symplocamide A

Sara C. Stolze; Michael Meltzer; Michael Ehrmann; Markus Kaiser

doi:10.1039/C0CC02889D

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Solid phase total synthesis of the 3-amino-6-hydroxy-2-piperidone (Ahp) cyclodepsipeptide and protease inhibitor Symplocamide A†‡

Sara C. Stolze,^ab Michael Meltzer,^b Michael Ehrmann^b and Markus Kaiser*^ab

Author affiliations

* Corresponding authors

^a Chemical Genomics Centre der Max-Planck-Gesellschaft, Otto-Hahn-Str. 15, 44227 Dortmund, Germany

^b Zentrum für Medizinische Biotechnologie, Fakultät Biologie und Geographie, Universität Duisburg-Essen, Universitätsstr. 2, 45117 Essen, Germany
E-mail: markus.kaiser@uni-due.de
Fax: +49 201 1833135
Tel: +49 201 1832969

Abstract

The solid phase total synthesis of the marine cyanobacterial Ahp-cyclodepsipeptide Symplocamide A is reported as a model for a general route for the synthesis of tailor-made non-covalent serine protease inhibitors.

This article is part of the themed collection: Enzymes and Proteins

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Supplementary files

Experimental details of the synthesis of compounds 1–13 and SymA on solid support
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Article information

DOI: https://doi.org/10.1039/C0CC02889D
Article type: Communication
Submitted: 29 Jul 2010
Accepted: 27 Sep 2010
First published: 22 Oct 2010

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Chem. Commun., 2010,46, 8857-8859

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Solid phase total synthesis of the 3-amino-6-hydroxy-2-piperidone (Ahp) cyclodepsipeptide and protease inhibitor Symplocamide A

S. C. Stolze, M. Meltzer, M. Ehrmann and M. Kaiser, Chem. Commun., 2010, 46, 8857 DOI: 10.1039/C0CC02889D

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Chemical Communications

Solid phase total synthesis of the 3-amino-6-hydroxy-2-piperidone (Ahp) cyclodepsipeptide and protease inhibitor Symplocamide A†‡

Abstract

Supplementary files

Article information

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Solid phase total synthesis of the 3-amino-6-hydroxy-2-piperidone (Ahp) cyclodepsipeptide and protease inhibitor Symplocamide A

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