Optimized FMOC solid-phase synthesis of thymosin 1 by side-chain anchoring onto a PEG Resin
Yésica García-Ramos 1 2, Matthieu Giraud 3, Judit Tulla-Puche 1 2 *, Fernando Albericio 1 2 4 *
1Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028-Barcelona, Spain
2CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park 08028-Barcelona, Spain
3Lonza Ltd, CH 3930, Visp, Switzerland
4Department of Organic Chemistry, University of Barcelona, 08028-Barcelona, Spain

email: Judit Tulla-Puche (judit.tulla@irbbarcelona.org) Fernando Albericio (albericio@irbbarcelona.org)

*Correspondence to Judit Tulla-Puche, Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028-Barcelona, Spain

*Correspondence to Fernando Albericio, Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028-Barcelona, Spain

Funded by:
CICYT; Grant Number: CTQ2009-07758
Generalitat de Catalunya; Grant Number: 2009SGR 1024


Abstract
Thymosin 1 is a 28-amino acid acetylated peptide used for the treatment of hepatitis B and C. This eptide has a difficult sequence because of the presence of consecutive -branched amino acids and shows a tendency to form -sheet structures, partly as a result of the many protecting groups required to assemble the peptide (up to 20 side-chain protecting groups). Consequently, its synthesis has been generally achieved by convergent solution chemistry. Here we report a straightforward stepwise solid-phase synthesis on a PEG solid-support that enables the scaling-up of this key therapeutic peptide. © 2009 Wiley Periodicals, Inc. Biopolymers (Pept Sci), 2009

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Received: 20 June 2009; Revised: 6 September 2009; Accepted: 21 September 2009