On-resin multicomponent 1,3-dipolar cycloaddition of cyclopentanone–proline enamines and sulfonylazides as an efficient tool for the synthesis of amidino depsipeptide mimics View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2019-11-28

AUTHORS

Raffaella Bucci, Federico Dapiaggi, Helena Macut, Stefano Pieraccini, Maurizio Sironi, Maria Luisa Gelmi, Emanuela Erba, Sara Pellegrino

ABSTRACT

Depsipeptides are biologically active peptide derivatives that possess a high therapeutic interest. The development of depsipeptide mimics characterized by a chemical diversity could lead to compounds with enhanced features and activity. In this work, an on-resin multicomponent procedure for the synthesis of amidino depsipeptide mimics is described. This approach exploits a metal-free 1,3-dipolar cycloaddition of cyclopentanone–proline enamines and sulfonylazides. In this reaction, the obtained primary cycloadduct undergoes a ring opening and molecular rearrangement giving access to a linear sulfonyl amidine functionalized with both a peptide chain and a diazoalkane. The so-obtained diazo function “one pot” reacts with the carboxylic group of N-Fmoc-protected amino acids leading to amidino depsipeptide mimics possessing a C4 aliphatic chain. An important advantage of this procedure is the possibility to easily obtain amidino-functionalized derivatives that are proteolytically stable peptide bond bioisosteres. Moreover, the conformational freedom given by the alkyl chain could promote the obtainment of cyclic depsipeptide with a stabilized secondary structure as demonstrated with both in silico calculations and experimental conformational studies. Finally, labeled depsipeptide mimics can be also synthesized using a fluorescent sulfonylazide in the multicomponent reaction. More... »

PAGES

15-24

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s00726-019-02805-3

DOI

http://dx.doi.org/10.1007/s00726-019-02805-3

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1122984157

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/31781906


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