title: Peptomeric analogues of trypsin inhibitor SFTI-1 isolated from sunflower seeds.
abstract: 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.
authors.affiliation: Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland. legowska@chem.univ.gda.pl
authors.forename: Anna
authors.initials: A
authors.lastname: Łegowska
authors.forename: Elzbieta
authors.initials: E
authors.lastname: Bulak
authors.forename: Magdalena
authors.initials: M
authors.lastname: Wysocka
authors.forename: Anna
authors.initials: A
authors.lastname: Jaśkiewicz
authors.forename: Adam
authors.initials: A
authors.lastname: Lesner
authors.forename: Dawid
authors.initials: D
authors.lastname: Debowski
authors.forename: Krzysztof
authors.initials: K
authors.lastname: Rolka
mesh_terms: 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
chemical_list: D019151:Peptide Library; D010456:Peptides, Cyclic; C448501:SFTI-1 peptide, sunflower; D014361:Trypsin Inhibitors; D014357:Trypsin