Search
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
Citations
-
7
CrossRef
-
0
Web of Science
-
7
Scopus
Authors (9)
-
D. Debowski
-
R. Łukajtis
-
M. Filipowicz
-
P. Strzelecka
-
M. Wysocka
-
A. Łęgowska
-
A. Lesner
-
K. Rolka
Cite as
Full text
full text is not available in portal
Keywords
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
seen 64 times
Recommended for you
Implication of the disulfide bridge in trypsin inhibitor SFTI-1 in its interaction with serine proteinases
- A. Łęgowska,
- D. Dębowski,
- Ł. Rafał
- + 4 authors
Fluorescent analogs of trypsin inhibitor SFTI-1 isolated from sunflower seeds-synthesis and applications
- A. Lesner,
- N. Karna,
- M. Psurski
- + 14 authors
Introduction of Pro and Its Analogues in the Conserved P1 Position of Trypsin Inhibitor SFTI-1 Retains Its Inhibitory Activity
- A. Legowska,
- D. Debowski,
- R. Lukajtis
- + 6 authors