Tetrahedron p. 9847 - 9864 (1994)
Update date:2022-08-04
Topics:
Neder, Karen M.
French, Stephanie A.
Miller, Stephen P. F.
Two fluorinatednonhydrolyzable analogs of myristoyl-coenzyme A were synthesized and tested for inhibitory activity against N-myristoyltransferase (NMT).S-(2,2-Difluoro-3-oxohexadecyl)-coenzyme A (3) and S-(3,3-difluoro-2-oxopentadecyl)-coenzyme A (2) were prepared by alkylation of coenzyme A and were purified by reverse phase chromatography.Inhibition of NMT was observed with 3 and 2, with IC50's of 110 nM and 80 nM, respectively, in an in vitro assay developed in our laboratory.The known unfluorinated analog S-(2-oxopentadecyl)-coenzyme A (1) was found to have an IC50 of 7 nM.At 100 μM in D2O, 3 was 59percent hydrated and 2 was 88percent hydrated.
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