Peptomeric analogues of trypsin inhibitor SFTI-1 isolated from sunflower seeds.
A series of linear and monocyclic analogues of trypsin inhibitor SFTI-1 isolated from sunflower seeds, modified by N-(4-aminobutyl)glycine (Nlys) and N-benzylglycine (Nphe), were obtained by the solid-phase method. Some of these peptomers displayed trypsin or chymotrypsin inhibitory activity. In contradiction to the literature data, in most analogues peptide bonds formed by these peptoid monomers were at least partially hydrolyzed by the experimental enzymes at two different pH (3.5 and 8.3). Nevertheless, the replacement of Phe present in the P(1) substrate specificity of linear inactive SFTI-1 analogue with Nphe, yielded a potent chymotrypsin inhibitor. The introduction of one cyclic element (a disulfide bridge or head-to-tail cyclization) to the analogues synthesized significantly increased their proteinase resistance.
Łegowska
Anna
A
Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland. legowska@chem.univ.gda.pl
Bulak
Elzbieta
E
Wysocka
Magdalena
M
Jaśkiewicz
Anna
A
Lesner
Adam
A
Debowski
Dawid
D
Rolka
Krzysztof
K
D000595:Amino Acid Sequence; D006368:Helianthus / Q000737:chemistry*; D006868:Hydrolysis; D008969:Molecular Sequence Data; D019151:Peptide Library; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D012639:Seeds / Q000737:chemistry*; D052616:Solid Phase Extraction / Q000379:methods; D013997:Time Factors; D014357:Trypsin / Q000187:drug effects; D014361:Trypsin Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D019151:Peptide Library; D010456:Peptides, Cyclic; C448501:SFTI-1 peptide, sunflower; D014361:Trypsin Inhibitors; D014357:Trypsin