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Synthesis 2019; 51(14): 2829-2838
DOI: 10.1055/s-0037-1612376
DOI: 10.1055/s-0037-1612376
paper
Microwave-Assisted Cyclization of Unprotected Dipeptides in Water to 2,5-Piperazinediones and Self-Assembly Study of Products and Reagents
Italian Ministry of University and Research (MIUR) through the Scientific Independence of Young Researchers (SIR) program (‘HOT-SPOT’ project, personal research grant no. RBSI14A7PL to S.M.), Ramón Areces Foundation (A.M.G.’s fellowship), and Beneficentia Stiftung Fundation.Further Information
Publication History
Received: 03 February 2019
Accepted after revision: 08 March 2019
Publication Date:
25 March 2019 (online)
Published as part of the Bürgenstock Special Section 2018 Future Stars in Organic Chemistry
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.
Key words
dipeptide - diketopiperazine - self-assembly - hydrogels - amyloid - microwaves - 2,5-piperazinedioneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1612376.
- Supporting Information
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