{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"omics_type":["Unknown"],"volume":["13"],"submitter":["Wunsch M"],"pubmed_abstract":["The amide moiety of peptides can be replaced for example by a triazole moiety, which is considered to be bioisosteric. Therefore, the carbonyl moiety of an amino acid has to be replaced by an alkyne in order to provide a precursor of such peptidomimetics. As most amino acids have a chiral center at C<sup>α</sup>, such amide bond surrogates need a chiral moiety. Here the asymmetric synthesis of a set of 24 <i>N</i>-sulfinyl propargylamines is presented. The condensation of various aldehydes with Ellman's chiral sulfinamide provides chiral <i>N-</i>sulfinylimines, which were reacted with (trimethylsilyl)ethynyllithium to afford diastereomerically pure <i>N</i>-sulfinyl propargylamines. Diverse functional groups present in the propargylic position resemble the side chain present at the C<sup>"],"journal":["Beilstein journal of organic chemistry"],"pagination":["2428-2441"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC5704752"],"repository":["biostudies-literature"],"pubmed_title":["Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics."],"pmcid":["PMC5704752"],"pubmed_authors":["Teichmann L","Neumann B","Schroder D","Wunsch M","Simon J","Frohr T","Klemme L","Hedwig S","Belu C","Heidemeyer S","Rudlof J","Sewald N","Stammler HG","Janson N","Holtkamp P","Hinzmann A"],"additional_accession":[]},"is_claimable":false,"name":"Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics.","description":"The amide moiety of peptides can be replaced for example by a triazole moiety, which is considered to be bioisosteric. Therefore, the carbonyl moiety of an amino acid has to be replaced by an alkyne in order to provide a precursor of such peptidomimetics. As most amino acids have a chiral center at C<sup>α</sup>, such amide bond surrogates need a chiral moiety. Here the asymmetric synthesis of a set of 24 <i>N</i>-sulfinyl propargylamines is presented. The condensation of various aldehydes with Ellman's chiral sulfinamide provides chiral <i>N-</i>sulfinylimines, which were reacted with (trimethylsilyl)ethynyllithium to afford diastereomerically pure <i>N</i>-sulfinyl propargylamines. Diverse functional groups present in the propargylic position resemble the side chain present at the C<sup>","dates":{"release":"2017-01-01T00:00:00Z","publication":"2017","modification":"2025-04-26T06:55:19.005Z","creation":"2019-03-27T03:03:08Z"},"accession":"S-EPMC5704752","cross_references":{"pubmed":["29234470"],"doi":["10.3762/bjoc.13.240"]}}