{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Chen H"],"funding":["U.S. Department of Health & Human Services | NIH | National Institute of General Medical Sciences","U.S. Department of Health & Human Services | NIH | National Institute of General Medical Sciences (NIGMS)","National Natural Science Foundation of China","NIGMS NIH HHS","National Natural Science Foundation of China (National Science Foundation of China)"],"pagination":["5372"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC11199569"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["15(1)"],"pubmed_abstract":["The synthesis of constrained 12-membered rings is notably difficult. The main challenges result from constraints during the linear peptide cyclization. Attempts to overcome constraints through excessive activation frequently cause peptidyl epimerization, while insufficient activation of the C-terminus hampers cyclization and promotes intermolecular oligomer formation. We present a β-thiolactone framework that enables the synthesis of cyclo-tetrapeptides via direct aminolysis. This tactic utilizes a mechanism that restricts C-terminal carbonyl rotation while maintaining high reactivity, thereby enabling efficient head-to-tail amidation, reducing oligomerization, and preventing epimerization. A broad range of challenging cyclo-tetrapeptides ( > 20 examples) are synthesized in buffer and exhi"],"journal":["Nature communications"],"pubmed_title":["Production of constrained L-cyclo-tetrapeptides by epimerization-resistant direct aminolysis."],"pmcid":["PMC11199569"],"funding_grant_id":["R35 GM138336","22122104","GM08500606A1","21933004","GM138336"],"pubmed_authors":["Wen Y","Fan X","Shekhtman A","Zhang Y","Lin Y","Xue XS","Chen H","Sciolino N","Breindel L","Dai Y","Zhang Q"],"additional_accession":[]},"is_claimable":false,"name":"Production of constrained L-cyclo-tetrapeptides by epimerization-resistant direct aminolysis.","description":"The synthesis of constrained 12-membered rings is notably difficult. The main challenges result from constraints during the linear peptide cyclization. Attempts to overcome constraints through excessive activation frequently cause peptidyl epimerization, while insufficient activation of the C-terminus hampers cyclization and promotes intermolecular oligomer formation. We present a β-thiolactone framework that enables the synthesis of cyclo-tetrapeptides via direct aminolysis. This tactic utilizes a mechanism that restricts C-terminal carbonyl rotation while maintaining high reactivity, thereby enabling efficient head-to-tail amidation, reducing oligomerization, and preventing epimerization. A broad range of challenging cyclo-tetrapeptides ( > 20 examples) are synthesized in buffer and exhi","dates":{"release":"2024-01-01T00:00:00Z","publication":"2024 Jun","modification":"2025-04-05T16:17:08.878Z","creation":"2025-02-19T00:16:57.697Z"},"accession":"S-EPMC11199569","cross_references":{"pubmed":["38918367"],"doi":["10.1038/s41467-024-49329-3"]}}