biostudies-literatureUnknown13Wunsch MThe 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^α, 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>Beilstein journal of organic chemistry2428-2441https://www.ebi.ac.uk/biostudies/studies/S-EPMC5704752biostudies-literatureAsymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics.PMC5704752Teichmann LNeumann BSchroder DWunsch MSimon JFrohr TKlemme LHedwig SBelu CHeidemeyer SRudlof JSewald NStammler HGJanson NHoltkamp PHinzmann AfalseAsymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics.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^α, 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>2017-01-01T00:00:00Z20172025-04-26T06:55:19.005Z2019-03-27T03:03:08ZS-EPMC57047522923447010.3762/bjoc.13.240