An improved method for the incorporation of fluoromethyl ketones into solid phase peptide synthesis techniques

An improved and expedient technique for the synthesis of peptidyl-fluoromethyl ketones is described. The methodology is based on prior coupling of an aspartate fluoromethyl ketone to a linker and mounting it onto resin-bound methylbenzhydrylamine hydrochloride. Subsequently, by utilising standard Fm...

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Bibliographic Details
Published in:RSC advances 2021-06, Vol.11 (33), p.2457-2464
Main Authors: Joshi, Dhira, Milligan, Jennifer C, Zeisner, Theresa U, O'Reilly, Nicola, Diffley, John F. X, Papageorgiou, George
Format: Article
Language:English
Subjects:
Chemistry
Ketones
Peptides
Protease inhibitors
Severe acute respiratory syndrome coronavirus 2
Solid phases
Synthesis
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Summary:An improved and expedient technique for the synthesis of peptidyl-fluoromethyl ketones is described. The methodology is based on prior coupling of an aspartate fluoromethyl ketone to a linker and mounting it onto resin-bound methylbenzhydrylamine hydrochloride. Subsequently, by utilising standard Fmoc peptide procedures, a number of short Z-protected peptides were synthesised and assessed as possible inhibitors of the main protease from SARS-CoV-2 (3CL pro ). An improved and expedient technique for the synthesis of peptidyl-fluoromethyl ketones is described.
ISSN:2046-2069
2046-2069
DOI:10.1039/d1ra03046a