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Development of oxetane modified building blocks for peptide synthesis
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Roesner, Stefan, Beadle, Jonathan D., Tam, Leo K. B., Wilkening, Ina, Clarkson, Guy J., Raubo, Piotr and Shipman, Michael (2020) Development of oxetane modified building blocks for peptide synthesis. Organic & Biomolecular Chemistry, 18 (28). pp. 5400-5405. doi:10.1039/D0OB01208D ISSN 1477-0520.
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WRAP-Development-oxetane-modified-building-blocks-peptide-synthesis-Shipman-2020.pdf - Accepted Version - Requires a PDF viewer. Download (1649Kb) | Preview |
Official URL: http://dx.doi.org/10.1039/D0OB01208D
Abstract
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: | Journal Article | |||||||||
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Subjects: | Q Science > QD Chemistry | |||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | |||||||||
Library of Congress Subject Headings (LCSH): | Peptides, Peptides -- Synthesis, Proteins -- Analysis, Pharmaceutical chemistry, Chemistry, Organic, Solid-phase synthesis | |||||||||
Journal or Publication Title: | Organic & Biomolecular Chemistry | |||||||||
Publisher: | Royal Society of Chemistry | |||||||||
ISSN: | 1477-0520 | |||||||||
Official Date: | 28 July 2020 | |||||||||
Dates: |
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Volume: | 18 | |||||||||
Number: | 28 | |||||||||
Page Range: | pp. 5400-5405 | |||||||||
DOI: | 10.1039/D0OB01208D | |||||||||
Status: | Peer Reviewed | |||||||||
Publication Status: | Published | |||||||||
Access rights to Published version: | Restricted or Subscription Access | |||||||||
Date of first compliant deposit: | 9 July 2020 | |||||||||
Date of first compliant Open Access: | 29 June 2021 | |||||||||
RIOXX Funder/Project Grant: |
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