Synlett 2013; 24(18): 2407-2410
DOI: 10.1055/s-0033-1339670
letter
© Georg Thieme Verlag Stuttgart · New York

Insight into β-Hairpin Stability: Interstrand Hydrogen Bonding

Emma Danelius
Department of Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, 412 96 Gothenburg, Sweden   Fax: +46(31)771394   Email: mate@chem.gu.se
,
Ulrika Brath
Department of Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, 412 96 Gothenburg, Sweden   Fax: +46(31)771394   Email: mate@chem.gu.se
,
Máté Erdélyi*
Department of Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, 412 96 Gothenburg, Sweden   Fax: +46(31)771394   Email: mate@chem.gu.se
› Author Affiliations
Further Information

Publication History

Received: 16 July 2013

Accepted: 02 August 2013

Publication Date:
28 August 2013 (online)


Abstract

For evaluation of the role of interstrand hydrogen bonding for β-hairpin stability, two cyclic peptides differing only in side chain hydroxy-to-methyl substitution were designed and synthesized on solid phase following the Fmoc–t-Bu–Trt protection strategy. Subsequent to cyclization in solution, combined computational and experimental ensemble analysis revealed higher conformational stability of the peptide capable of interstrand hydrogen bonding.

Supporting Information

 
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