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Organic synthesis

A higher-yield route to FP–PEG–biotin ABPP probe

Xu H, Sabit H, Amidon GL, et al. · Beilstein journal of organic chemistry · 2013

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%.

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.

How this study connects

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