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Accordingly, the synthesis of lipoylated peptides as diagnostic tools is a relevant target. Up to now, the proper tools for the introduction of lipoylation on building blocks to be used in Fmoc\/tBu solid phase peptide synthesis (SPPS) are lacking, and the role of chirality in lipoylation remains poorly studied.<\/jats:p><jats:p>In this paper, we present the synthesis of lipoylated lysine derivatives as pure diastereomeric building blocks suitable for Fmoc\/tBu SPPS and their introduction in relevant peptide sequences to possibly serve as synthetic probes for the development of novel diagnostic tools for this disease.<\/jats:p><jats:p>The optimization of the synthesis of lipoylated building blocks derived from racemic, (<jats:italic>R<\/jats:italic>)\u2010, and (<jats:italic>S<\/jats:italic>)\u2010\u03b1\u2010lipoic acid is described. Synthesis of peptide probes incorporating lipoylation is described. An insight regarding the cleavage of lipoylated peptides is given, as well as a method to oxidize or reduce the 1,2\u2010dithiolane ring of the lipoyl moiety directly on the peptide without any subsequent purification. Copyright \u00a9 2015 European Peptide Society and John Wiley &amp; Sons, Ltd.<\/jats:p>","DOI":"10.1002\/psc.2761","type":"journal-article","created":{"date-parts":[[2015,3,27]],"date-time":"2015-03-27T08:57:57Z","timestamp":1427446677000},"page":"408-414","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Synthesis of diastereomerically pure Lys(<i>N<\/i><sup>\u03b5<\/sup>\u2010lipoyl) building blocks and their use in Fmoc\/tBu solid phase synthesis of lipoyl\u2010containing peptides for diagnosis of primary biliary cirrhosis"],"prefix":"10.1002","volume":"21","author":[{"given":"C\u00e9dric","family":"Rentier","sequence":"first","affiliation":[{"name":"French\u2010Italian Interdepartmental Laboratory of Peptide and Protein Chemistry &amp; Biology\u2009\u2010\u2009PeptLab"},{"name":"Laboratoire de Chimie Biologique EA4505 University of Cergy\u2010Pontoise  5 mail Gay\u2010Lussac, Neuville\u2010sur\u2010Oise 95000 Cergy\u2010Pontoise France"},{"name":"Department of Chemistry \u201cUgo Schiff\u201d University of Florence  Via della Lastruccia 3\/13 I\u201050019 Sesto Fiorentino Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Giulia","family":"Pacini","sequence":"additional","affiliation":[{"name":"French\u2010Italian Interdepartmental Laboratory of Peptide and Protein Chemistry &amp; Biology\u2009\u2010\u2009PeptLab"},{"name":"Department NeuroFarBa, Section of Pharmaceutical and Nutraceutical Sciences University of Florence, Via Ugo Schiff 6  I\u201050019 Sesto Fiorentino Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Francesca","family":"Nuti","sequence":"additional","affiliation":[{"name":"French\u2010Italian Interdepartmental Laboratory of Peptide and Protein Chemistry &amp; Biology\u2009\u2010\u2009PeptLab"},{"name":"Department of Chemistry \u201cUgo Schiff\u201d University of Florence  Via della Lastruccia 3\/13 I\u201050019 Sesto Fiorentino 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