{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"omics_type":["Unknown"],"volume":["20"],"submitter":["van der Heide P"],"pubmed_abstract":["The rising popularity of bioconjugate therapeutics has led to growing interest in late-stage functionalization (LSF) of peptide scaffolds. α,β-Unsaturated amino acids like dehydroalanine (Dha) derivatives have emerged as particularly useful structures, as the electron-deficient olefin moiety can engage in late-stage functionalization reactions, like a Giese-type reaction. Cheap and widely available building blocks like organohalides can be converted into alkyl radicals by means of photoinduced silane-mediated halogen-atom transfer (XAT) to offer a mild and straightforward methodology of alkylation. In this research, we present a metal-free strategy for the photochemical alkylation of dehydroalanine derivatives. Upon abstraction of a hydride from tris(trimethylsilyl)silane (TTMS) by an exci"],"journal":["Beilstein journal of organic chemistry"],"pagination":["3274-3280"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC11665442"],"repository":["biostudies-literature"],"pubmed_title":["Giese-type alkylation of dehydroalanine derivatives via silane-mediated alkyl bromide activation."],"pmcid":["PMC11665442"],"pubmed_authors":["Luridiana A","Piersanti G","Retini M","Fanini F","Noel T","van der Heide P","Mazzarella D","Secci F"],"additional_accession":[]},"is_claimable":false,"name":"Giese-type alkylation of dehydroalanine derivatives via silane-mediated alkyl bromide activation.","description":"The rising popularity of bioconjugate therapeutics has led to growing interest in late-stage functionalization (LSF) of peptide scaffolds. α,β-Unsaturated amino acids like dehydroalanine (Dha) derivatives have emerged as particularly useful structures, as the electron-deficient olefin moiety can engage in late-stage functionalization reactions, like a Giese-type reaction. Cheap and widely available building blocks like organohalides can be converted into alkyl radicals by means of photoinduced silane-mediated halogen-atom transfer (XAT) to offer a mild and straightforward methodology of alkylation. In this research, we present a metal-free strategy for the photochemical alkylation of dehydroalanine derivatives. Upon abstraction of a hydride from tris(trimethylsilyl)silane (TTMS) by an exci","dates":{"release":"2024-01-01T00:00:00Z","publication":"2024","modification":"2025-04-18T12:46:04.579Z","creation":"2025-04-06T22:11:49.639Z"},"accession":"S-EPMC11665442","cross_references":{"pubmed":["39717264"],"doi":["10.3762/bjoc.20.271"]}}