Formation of Diastereoisomeric Piperazine-2,5-dione from dl-Alanine in the Presence of Olivine and Water

Shigeshi Fuchida, Hiroshi Naraoka, Harue Masuda

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

dl-Alanine (Ala) was heated with/without powdered olivine and water at 120 °C for 8 days to investigate the formation of the diastereoisomers of piperazine-2,5-dione (diketopiperazine, DKP). When only dl-Ala was heated with a small amount of water, 3.0 % of dl-Ala changed to cis- and trans-DKP after 8 days. DKPs were not detected after heating when no water was added. The presence of a small amount of water is important factor controlling peptide production rates under thermal conditions. When DL-Ala was heated with olivine powder for 8 days, the yields of cis- and trans-DKP were 6.8 and 4.9 %, respectively. The high yield of cis-DKP compared with trans-DKP was attributed to greater thermal stability of cis-DKP. After heating for 8 days, the diastereoisomeric excess of cis-DKP without olivine was 7.3 %, whereas a much higher value of 16.3 % was obtained in the presence of olivine. Taken together, these results show that olivine is not only an efficient catalyst for the formation of DKPs but that it also play a significant role in determining the diastereoisomer selectivity of these cyclic dipeptides.

Original languageEnglish
Pages (from-to)83-92
Number of pages10
JournalOrigins of Life and Evolution of Biospheres
Volume47
Issue number1
DOIs
Publication statusPublished - Mar 1 2017

All Science Journal Classification (ASJC) codes

  • Ecology, Evolution, Behavior and Systematics
  • Space and Planetary Science

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