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A higher-yield route to FP–PEG–biotin ABPP probe
Reworking Cravatt’s FP–PEG–biotin synthesis cuts chromatography and raises overall yield from 1% to 28.5%.
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How does the new FP–PEG–biotin route compare in yield?
28.5% overall over nine steps versus 1% in the Cravatt sequence.
Source: An improved synthesis of a fluorophosphonate-polyethylene glycol-biotin probe and its use against competitive substrates · DOI · quote verified
How many chromatographies does the new route need?
Four over nine steps versus six over eight steps previously.
Source: An improved synthesis of a fluorophosphonate-polyethylene glycol-biotin probe and its use against competitive substrates · DOI · quote verified
What yield was reported for iodide 4b?
Combined 90% from tosylation plus Finkelstein.
Source: An improved synthesis of a fluorophosphonate-polyethylene glycol-biotin probe and its use against competitive substrates · DOI · quote verified
What yield did the Arbuzov step give?
92% of phosphonate 5 after 1 h in neat P(OEt)3.
Source: An improved synthesis of a fluorophosphonate-polyethylene glycol-biotin probe and its use against competitive substrates · DOI · quote verified
What yield was hydrogenolysis to alcohol 6?
96%.
Source: An improved synthesis of a fluorophosphonate-polyethylene glycol-biotin probe and its use against competitive substrates · DOI · quote verified
What yield was succinimidyl carbonate 7?
87% after chromatography.
Source: An improved synthesis of a fluorophosphonate-polyethylene glycol-biotin probe and its use against competitive substrates · DOI · quote verified
What yield was biotin coupling to 8?
76% after purification.
Source: An improved synthesis of a fluorophosphonate-polyethylene glycol-biotin probe and its use against competitive substrates · DOI · quote verified
How is the fluorophosphonate installed?
DAST in dichloromethane at −42 °C, 80% yield of probe 1.
Source: An improved synthesis of a fluorophosphonate-polyethylene glycol-biotin probe and its use against competitive substrates · DOI · quote verified
Was crude 1 usable in biology?
Yes: 80% yield material was pure enough to use directly in biological studies.
Source: An improved synthesis of a fluorophosphonate-polyethylene glycol-biotin probe and its use against competitive substrates · DOI · quote verified
What enzyme class does the probe engage?
Serine hydrolases from several proteome samples, including rat tissues.
Source: An improved synthesis of a fluorophosphonate-polyethylene glycol-biotin probe and its use against competitive substrates · DOI · quote verified
Who first made FP–PEG–biotin 1?
The Cravatt group, for avidin pull-down and MS.
Source: An improved synthesis of a fluorophosphonate-polyethylene glycol-biotin probe and its use against competitive substrates · DOI · quote verified