Organic synthesis
A higher-yield route to FP–PEG–biotin ABPP probe
Open access · cc by · source: Europe PMC
Reworking Cravatt’s FP–PEG–biotin synthesis cuts chromatography and raises overall yield from 1% to 28.5%.
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A higher-yield route to FP–PEG–biotin ABPP probe
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The new route gives 28.5% overall yield of 1 over nine steps.
Starting from common precursor 2 , our synthesis requires only four chromatographic purifications over nine steps and provides a 28.5% overall yield of 1 .
The Cravatt sequence had an overall yield of 1%.
In contrast, the Cravatt sequence requires six chromatographic purifications over eight steps with an overall yield of 1%.
Key findings
Nine steps, four chromatographies, 28.5% overall yield versus six chromatographies/eight steps and 1% in the original sequence. Key steps: 90% to iodide 4b, 92% Arbuzov, 96% debenzylation, 87% carbonate, 76% biotin coupling, 80% DAST. The probe labels serine hydrolases in proteomes.
Methodology
Authors redesigned the route from tetraethylene glycol via tosylate/iodide, Arbuzov phosphonate, hydrogenolysis, succinimidyl carbonate, biotin coupling, and DAST fluorination, then tested the probe on serine hydrolases and reversible-substrate competition.
Limitations
Competition with reversible substrates is preliminary; this is not a new enzyme-inhibitor campaign with full Ki tables.
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