Department of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy.
Organic and Biomimetic Chemistry Research Group, Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281-S4, 9000 Ghent, Belgium.
Org Lett. 2023 Sep 15;25(36):6618-6622. doi: 10.1021/acs.orglett.3c02289. Epub 2023 Sep 1.
1,4-Dione-containing peptides are generated during the cleavage of 2,5-disubstituted furan-containing systems. The generated electrophilic systems then react with α-effect nucleophiles, following a Paal-Knorr-like mechanism, for the generation of macrocyclic peptides, occurring after simple resuspension of the crude peptide in water. Conveniently, the in situ generation of the electrophile from a stable furan ring avoids the complications associated with the synthesis of carbonyl-containing peptides. Detailed investigation of the reaction characteristics was first performed on supramolecular coiled-coil systems.
1,4-二酮肽是在 2,5-二取代呋喃体系的裂解过程中产生的。生成的亲电体系随后与α-效应亲核试剂发生反应，遵循 Paal-Knorr 类似的机制，生成大环肽，在将粗肽简单地重新悬浮在水中后即可发生。方便的是，从稳定的呋喃环原位生成亲电体避免了与含羰基肽合成相关的复杂问题。首先对超分子螺旋螺旋体系的反应特性进行了详细的研究。
