Increasing the conformational diversity of peptides with non-proteinogenic amino acids (INCONDI)
Croatian Science Foundation IP-2022-10-9617
12/2023 - 12/2027
This project aims to expand the chemical space of NPAAs that could modulate peptide conformation in a defined and predictable way. This will be achieved by: (i) the synthesis of NPAAs derived from carbohydrates, carbasugars and heteroaromatic compounds, (ii) the synthesis of peptides with incorporated NPAAs and their structural characterization, and (iii) the determination of the non-covalent interactions involving NPAAs that are responsible for the adoption of a particular secondary structure. The inspiration for NPAAs is found in natural compounds equipped with well-defined three-dimensional scaffolds. The envisaged methodology is based on the chemical transformation of carbohydrates, carbasugars and heteroaromatic compounds into related amino acids. We anticipate that peptides with such NPAAs will adopt conformationally distinct secondary structures. We plan to determine the role of structure, stereochemistry and non-covalent interactions responsible for their stabilization.
Team:
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Mateja Matišić Markić
Postdoc
Antonija Ožegović
Postdoc
Franko Pahović
PhD student
David Šterpin
PhD student
Josipa Suć Sajko
Senior Professional
Associate
Lidija Brkljačić
Senior Professional
Associate
Barbara Bogović
Senior Professional
Associate
Publications:
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Josipa Suć Sajko, Franko Pahović and Ivanka Jerić, 5-Amino-5-deoxyshikimic acid as a versatile g-amino acid for peptidomimetic synthesis, ACS Omega, 11(9) (2026) 15559–15565
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Barbara Bogović, Ivana Colić, Ivana Nikšić-Franjić, Vilko Smrečki and Ivanka Jerić, C-Glycosyl α-Amino Acids as Structural Encoders of Peptide Conformation, Angew. Chem. Int. Ed. 65 (2026) e22704
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I. Colić, B. Bogović, I. Jerić, The synthesis of oligomers containing alternating C-glycosyl α-amino acids and proteinogenic α-amino acids. New J. Chem. 48 (2024) 12584 - 12590
Conferences:
Jerić, Ivanka; Bogović, Barbara; Nikšić-Franjić, Ivana
C-Glycosyl α-Amino Acids as Structural Encoders of Peptide Conformation // 38th European Peptide Symposium
Beč, Austrija, 06.09.2026-11.09.2026
Pahović, Franko, Jerić, Ivanka
Substrate-Controlled Asymmetric Synthesis of Polyhydroxylated Cyclic Vinyl Triflates// 19th Belgian Organic Synthesis Symposium
Leuven, Belgija, 05.07.2026-10.07.2026
Matišić, Mateja; Šterpin, David; Pahović, Franko; Glavaš, Mladena; Nikšić-Franjić, Ivana; Jerić, Ivanka
Probing carbohydrate–aromatic interactions in aqueous solution using non-proteinogenic (hetero)aromatic amino acids // 19th Belgian Organic Synthesis Symposium, Leuven, Belgija, 05.07.2026-10.07.2026
Pahović, Franko; Suć Sajko, Josipa; Jerić, Ivanka
Synthesis of potential urea organocatalyst from D-(−)-quinic acid // XLIX “A. “Corbella”International Summer School on Organic Synthesis, 2025, Gargnano, Italy
Pahović, Franko; Suć Sajko, Josipa; Jerić, Ivanka
Preparation of a potential urea-based organocatalyst from D-(−)-quinic acid // 29th Croatian Meeting of Chemists and Chemical Engineers and 7th Symposium Vladimir Prelog, 2025, Split, Croatia
Fmoc Solid-Phase Synthesis and Structural Characterization of C-Glycopeptides // 29th Croatian Meeting of Chemists and Chemical Engineers and 7th Symposium Vladimir Prelog, 2025, Split, Croatia
Suć Sajko, Josipa, Jerić, Ivanka
Conformational and functional diversification of peptides induced by aminoshikimic acid // 25th Tetrahedron Symposium, 2025, Brugge, Belgium
Jerić, Ivanka; Bogović, Barbara
Synthesis and conformational analysis of oligomers containing C-glycosyl amino acids // European Symposium on Organic Chemistry, 2025, Copenhagen, Denmark
Franko presented his work at Josipa presented her work at
ISOS 2025 Tetrahedron Conference 2025
Barbara at Croatian Meeting of Chemists and Chemical Engineers in Split (2025)