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Photocatalyzed Oxidative Decarboxylation Forming Aminovinylcysteine Containing Peptides
oleh: Masaya Kumashiro, Kosuke Ohsawa, Takayuki Doi
Format: | Article |
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Diterbitkan: | MDPI AG 2022-12-01 |
Deskripsi
The formation of (2<i>S</i>,3<i>S</i>)-<i>S</i>-[(<i>Z</i>)-aminovinyl]-3-methyl-D-cysteine (AviMeCys) substructures was developed based on the photocatalyzed-oxidative decarboxylation of lanthionine-bearing peptides. The decarboxylative selenoetherification of the <i>N</i>-hydroxyphthalimide ester, generated in situ, proceeded under mild conditions at −40 °C in the presence of 1 mol% of eosin Y-Na<sub>2</sub> as a photocatalyst and the Hantzsch ester. The following β-elimination of the corresponding <i>N</i>,<i>Se</i>-acetal was operated in a one-pot operation, led to AviMeCys substructures found in natural products in moderate to good yields. The sulfide-bridged motif, and also the carbamate-type protecting groups, such as Cbz, Teoc, Boc and Fmoc groups, were tolerant under the reaction conditions.