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Synthesis 2009(1): 143-147  
DOI: 10.1055/s-0028-1083281
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Fmoc-Pro-Hyp(TBDPS)-Gly-OH and Its Application as a Versatile Building Block for the Preparation of Collagen Model Peptides

Roman S. Erdmann, Helma Wennemers*
Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland
Fax: +41(61)2670976; e-Mail: Helma.Wennemers@unibas.ch;
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Publication History

Received 20 October 2008
Publication Date:
12 December 2008 (online)

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Abstract

The efficient synthesis of the tripeptidic building block Fmoc-Pro-Hyp(TBDPS)-Gly-OH and its application for the preparation of collagen model peptides (CMPs) has been achieved. The silyl ether protecting group prevents undesired side reactions during the CMP synthesis thereby facilitating purification and allowing for selective deprotection of the hydroxyproline residue without affecting the solid-supported CMP.

Key words

collagen - peptides - protecting groups - solid-phase synthesis - TBDPS silyl ether

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