Journal of Organic Chemistry p. 1882 - 1887 (1981)
Update date:2022-08-05
Topics:
Rastetter, William H.
Adams, Julian
A model system for the involvement of lipoic acid in α-keto acid dehydrogenase systems is described. 2-(α-Hydroxyethyl)-3-benzyl-4-methylthiazolium tetrafluoroborate (6) serves as precursor for an analogue of the thiamine-bound active aldehyde 1 in the natural system.The model active aldehyde 7 reacts with linear disulfides, yielding thiols and thioesters.The 1,2-dithiolane, methyl lipoate (14), is unreactive under model reaction conditions.The tetrahedral intermediate which would be formed from methyl lipoate (14) plus an active aldehyde analogue 19 has been generated in a nonbiomimetic fashion.The synthetic tetrahedral intermediate 17 undergoes the reverse of the biological, disulfide reductive cleavage reaction.
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Doi:10.1016/j.tetlet.2020.152097
(2020)Doi:10.1021/acs.orglett.0c02229
(2020)Doi:10.1055/s-1992-26228
(1992)Doi:10.1039/DT9790000134
()Doi:10.1021/ja00960a029
(1966)Doi:10.1055/s-1981-29607
(1981)
