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Hydrothermal, catalyst-free production of a cyclic dipeptide from lysine

Fan, Yujie 1; Hoffmann, Alexander 1; Hornung, Ursel 1; Raffelt, Klaus 1; Zevaco, Thomas A. ORCID iD icon 1; Dahmen, Nicolaus 1
1 Institut für Katalyseforschung und -technologie (IKFT), Karlsruher Institut für Technologie (KIT)

Abstract:

The formation of cyclic dipeptides, 2,5-diketopiperazines (DKP), from lysine in aqueous solution was investigated at hydrothermal conditions (250 to 350 °C) without the addition of catalyst. The products obtained were analyzed by GC–MS combined with extensive $^{1}$H,$^{13}$C NMR analysis, after purification via preparative chromatography. The main product of the conversion of lysine, octahydrodipyrido[1,2-a:1',2'-d]pyrazine-6,12(2H,6aH)-dione, was successfully isolated and identified. The purification/separation protocol is rapid, environmentally friendly, and highly efficient with excellent selectivity (81 wt%) in the oils obtained from the conversion of lysine at 300 °C. Performing the conversion step at higher temperatures or lysine concentrations led to the formation of complicated side products. Based on the evolution of key compounds during hydrothermal conversion of lysine, we propose a tentative mechanism for the formation of diketopiperazine. The technique presented in this work provides a novel catalyst-free pathway for the synthesis of DKP.


Verlagsausgabe §
DOI: 10.5445/IR/1000152867/pub
Veröffentlicht am 24.11.2022
Postprint §
DOI: 10.5445/IR/1000152867
Veröffentlicht am 18.11.2022
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Katalyseforschung und -technologie (IKFT)
Publikationstyp Zeitschriftenaufsatz
Publikationsmonat/-jahr 11.2022
Sprache Englisch
Identifikator ISSN: 0165-2370
KITopen-ID: 1000152867
HGF-Programm 38.05.01 (POF IV, LK 01) Anthropogenic Carbon Cycle
Erschienen in Journal of Analytical and Applied Pyrolysis
Verlag Elsevier
Band 168
Seiten Art.-Nr.: 105792
Vorab online veröffentlicht am 17.11.2022
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