Microwave-Assisted Cyclization of Unprotected Dipeptides in Water to 2,5-Piperazinediones and Self-Assembly Study of Products­ and Reagents

Abstract Dipeptides and their cyclized 2,5-piperazinedione (or diketopiperazine, DKP) derivatives are attractive building blocks for supra­molecular hydrogels. The Phe-Phe, ( p -nitro)-Phe-Phe, and Phe-Val dipeptides and their corresponding DKPs are studied for self-assembly in water. The DKPs were...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2019-07, Vol.51 (14), p.2829-2838
Main Authors: Kurbasic, Marina, Semeraro, Sabrina, Garcia, Ana M., Kralj, Slavko, Parisi, Evelina, Deganutti, Caterina, De Zorzi, Rita, Marchesan, Silvia
Format: Article
Language:English
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Summary:Abstract Dipeptides and their cyclized 2,5-piperazinedione (or diketopiperazine, DKP) derivatives are attractive building blocks for supra­molecular hydrogels. The Phe-Phe, ( p -nitro)-Phe-Phe, and Phe-Val dipeptides and their corresponding DKPs are studied for self-assembly in water. The DKPs were obtained in high yields by microwave-assisted cyclization­ of the dipeptides in water, demonstrating that use of their methyl ester derivatives as reported in the literature is not necessary for successful cyclization. Single-crystal XRD structures are reported for two DKPs as well as stable hydrogels at neutral pH.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0037-1612376