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

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.



Titolo: Microwave-Assisted Cyclization of Unprotected Dipeptides in Water to 2,5-Piperazinediones and Self-Assembly Study of Products­ and Reagents
Autori: 
KURBASIC, MARINA
SEMERARO, SABRINA
GARCIA FERNANDEZ, ANA MARIA
KRALJ, SLAVKO
PARISI, EVELINA
DEGANUTTI, CATERINA
DE ZORZI, RITA
MARCHESAN, SILVIA (Corresponding)
Data di pubblicazione: 2019
Stato di pubblicazione: Pubblicato
Rivista: 
SYNTHESIS  
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.
Handle: http://hdl.handle.net/11368/2945253
Digital Object Identifier (DOI): http://dx.doi.org/10.1055/s-0037-1612376
URL: https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0037-1612376
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