通过甘氨酰异羟肟酸的Lossen重排实现的沙克替宁连接的后期形成。
Late-Stage Formation of a Sactionine Linkage Enabled by Lossen Rearrangement of Glycyl Hydroxamic Acid.
作者信息
Hayashi Junya, Kobayashi Daishiro, Denda Masaya, Otaka Akira
机构信息
Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima 770-8505, Japan.
出版信息
Org Lett. 2024 Jun 21;26(24):5167-5171. doi: 10.1021/acs.orglett.4c01685. Epub 2024 Jun 7.
Late-stage formation of a sactionine thioether bond connecting a Gly α-carbon and Cys thiol was achieved by Lossen rearrangement of a glycyl hydroxamic acid (GlyHA) residue in a peptide. Lossen rearrangement allowed conversion of GlyHA within a peptide to an -acyl iminium equivalent, which subsequently reacted with -acetamidomethyl Cys (Cys(Acm)) in TFA in the presence of guanidine hydrochloride (Gn·HCl) to yield the desired thioether linkage in the final stage.
通过肽中甘氨酰异羟肟酸（GlyHA）残基的洛森重排，实现了连接甘氨酸α-碳和半胱氨酸硫醇的硫代环丁烷硫醚键的后期形成。洛森重排使肽中的GlyHA转化为酰基亚胺离子等价物，该等价物随后在盐酸胍（Gn·HCl）存在下于三氟乙酸中与乙酰氨基甲基半胱氨酸（Cys(Acm)）反应，在最后阶段生成所需的硫醚键。
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