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Development of oxetane modified building blocks for peptide synthesis

Roesner, S, Beadle, JD, Tam, LKB, Wilkening, I, Clarkson, GJ, Raubo, P and Shipman, M (2020) Development of oxetane modified building blocks for peptide synthesis. Organic and Biomolecular Chemistry, 18 (28). pp. 5400-5405. ISSN 1477-0520

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The synthesis and use of oxetane modified dipeptide building blocks in solution and solid-phase peptide synthesis (SPPS) is reported. The preparation of building blocks containing non-glycine residues at the N-terminus in a stereochemically controlled manner is challenging. Here, a practical 4-step route to such building blocks is demonstrated, through the synthesis of dipeptides containing contiguous alanine residues. The incorporation of these new derivatives at specific sites along the backbone of an alanine-rich peptide sequence containing eighteen amino acids is demonstrated via solid-phase peptide synthesis. Additionally, new methods to enable the incorporation of all 20 of the proteinogenic amino acids into such dipeptide building blocks are reported through modifications of the synthetic route (for Cys and Met) and by changes to the protecting group strategy (for His, Ser and Thr).

Item Type: Article
Uncontrolled Keywords: Ethers, Cyclic; Dipeptides; Molecular Structure; Solid-Phase Synthesis Techniques; Drug Development; Dipeptides; Drug Development; Ethers, Cyclic; Molecular Structure; Solid-Phase Synthesis Techniques; 0304 Medicinal and Biomolecular Chemistry; 0305 Organic Chemistry; Organic Chemistry
Subjects: Q Science > QD Chemistry
R Medicine > RS Pharmacy and materia medica
Divisions: Pharmacy & Biomolecular Sciences
Publisher: Royal Society of Chemistry
SWORD Depositor: A Symplectic
Date Deposited: 23 Apr 2024 15:52
Last Modified: 23 Apr 2024 16:00
DOI or ID number: 10.1039/D0OB01208D
URI: https://researchonline.ljmu.ac.uk/id/eprint/23115
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