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Implication of the disulfide bridge in trypsin inhibitor SFTI-1 in its interaction with serine proteinases
Abstract
Fourteen monocyclic analogues of trypsin inhibitor SFTI-1 isolated from sunflower seeds were synthesized by the solid-phase method. The purpose of this work was to establish the role of a disulfide bridge present in inhibitor's side chains of Cys3 and Cys11 in association with serine proteinases. This cyclic fragment was replaced by the disulfide bridges formed by L-pencillamine (Pen), homo-L-cysteine (Hcy), N-sulfanylethylglycine (Nhcy) or combination of the three with Cys. As in the substrate specificity the P(1) position of the synthesized analogues Lys, Nlys [N-(4-aminobutyl) glycine], Phe or Nphe (N-benzylglycine) were present, and they were checked for trypsin and chymotrypsin inhibitory activity. The results clearly indicated that Pen and Nhcy were not acceptable at the position 3, yielding inactive analogues, whereas another residue (Cys11) could be substituted without any significant impact on the affinity towards proteinase. On the other hand, elongation of the Cys3 side chain by introduction of Hcy did not affect inhibitory activity, and an analogue with the Hcy-Hcy disulfide bridge was more than twice as effective as the reference compound ([Phe(5)] SFTI-1) in inhibition of bovine alpha-chymotrypsin. (C) 2010 Elsevier Ltd. All rights reserved.
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Authors (7)
-
Anna Łęgowska
- Wydział Chemii UG Katedra Chemii Bioorganicznej
-
Dawid Dębowski
- Wydział Chemii UG Katedra Chemii Bioorganicznej
-
Łukajtis Rafał
- Wydział Chemii UG Katedra Chemii Bioorganicznej
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Magdalena Wysocka
- Wydział Chemii UG Katedra Chemii Bioorganicznej
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Cezary Czaplewski Dr hab.
- Wydział Chemii UG Katedra Chemii Teoretycznej
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Krzysztof Rolka
- Wydział Chemii UG Katedra Chemii Bioorganicznej
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Details
- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
BIOORGANIC & MEDICINAL CHEMISTRY
no. 18,
edition 23,
pages 8188 - 8193,
ISSN: 0968-0896 - Language:
- English
- Publication year:
- 2010
- Bibliographic description:
- Łęgowska A., Dębowski D., Rafał Ł., Wysocka M., Czaplewski C., Lesner A., Rolka K.: Implication of the disulfide bridge in trypsin inhibitor SFTI-1 in its interaction with serine proteinases// BIOORGANIC & MEDICINAL CHEMISTRY. -Vol. 18, iss. 23 (2010), s.8188-8193
- DOI:
- Digital Object Identifier (open in new tab) 10.1016/j.bmc.2010.10.014
- Verified by:
- Gdańsk University of Technology
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