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Hybrid analogues of SFTI-1 modified in P1 position by β- and γ-amino acids and N-substituted β-alanines
Abstract
A series of compounds containing either non-proteinogenic beta-/gamma-amino acids or N-substituted beta-alanine residues (beta-peptoid units) in P-1 specificity position were synthesized based on the structure of sunflower trypsin inhibitor 1 (SFTI-1). The compounds were synthesized on a solid support; the N-substituted beta-alanines (beta Nhlys and beta Nhphe) were introduced into a peptidomimetic chain via a two-step approach using acryloyl chloride and an appropriate primary amine. The inhibitory activities were characterized in vitro against bovine alpha-chymotrypsin or bovine beta-trypsin. Three analogues displayed activity comparable to fully proteinogenic counterparts-monocyclic SFTI-1 and [Phe(5)] SFTI-1. Moreover, all active peptidomimetics were resistant toward proteolytic degradation, even after 24-h incubation at room temperature. (C) 2012 Wiley Periodicals, Inc
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Authors (9)
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D. Debowski
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R. Łukajtis
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M. Filipowicz
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P. Strzelecka
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M. Wysocka
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A. Łęgowska
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A. Lesner
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K. Rolka
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Details
- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
BIOPOLYMERS
no. 100,
edition 2,
pages 154 - 159,
ISSN: 0006-3525 - Language:
- English
- Publication year:
- 2013
- Bibliographic description:
- Debowski D., Łukajtis R., Filipowicz M., Strzelecka P., Wysocka M., Łęgowska A., Lesner A., Rolka K.: Hybrid analogues of SFTI-1 modified in P1 position by β- and γ-amino acids and N-substituted β-alanines// BIOPOLYMERS. -Vol. 100, iss. 2 (2013), s.154-159
- DOI:
- Digital Object Identifier (open in new tab) 10.1002/bip.22184
- Verified by:
- Gdańsk University of Technology
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