ArticleACS combinatorial science2016
Click-Based Libraries of SFTI-1 Peptides: New Methods Using Reversed-Phase Silica.
Article in ACS combinatorial science, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Synthetic Elaboration of Native DNA by RASS (SENDR).ACS central science · 2020Article
- RASS-Enabled S/P-C and S-N Bond Formation for DEL Synthesis.Angewandte Chemie (International ed. in English) · 2020Article
- Expanding Reactivity in DNA-Encoded Library Synthesis via Reversible Binding of DNA to an Inert Quaternary Ammonium Support.Journal of the American Chemical Society · 2019Article
- Post-Translational Backbone Engineering through Selenomethionine-Mediated Incorporation of Freidinger Lactams.Angewandte Chemie (International ed. in English) · 2018Article
- Advancing the Frontiers of Chemical Protein Synthesis-The 7Cell chemical biology · 2018Article
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Authors and funding
2 authors.
Funding
Abstract
Performing sequential reactions for the orthogonal derivatization of peptides in solution often requires intermediate handling and purification steps. To solve these problems, we have exploited the distinct adsorption kinetics of peptides toward particulate reversed-phase (RP) C18 silica material, enabling consecutive reactions to be performed without intermediate elution. To illustrate this approach, sequential CuAAC/click reactions were used to modify an analog of the bicyclic peptide sunflower trypsin inhibitor 1 (SFTI-1), a potent scaffold for trypsin and chymotrypsin-like enzyme inhibitors. The SFTI-1 scaffold was synthesized containing both β-azido alanine and propargyl glycine residues. Despite the mutual reactivity of these groups, site isolation on RP silica enabled consecutive click reactions and associated washing steps to be performed while the peptide remained immobilized. Importantly, this approach eliminated side products that could form between two peptides or within a single peptide. These studies suggest a broad utility for RP silica in solving both peptide handling problems and in improving synthetic workflows.
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