Diketopiperazine-based polymers from common amino acids

Abstract

High‐melting‐point polymers with heterocyclic backbone units were synthesized from common amino acids. Acids were first converted to methyl ester salts and then were dimerized to form diketopiperazines, which were polymerized in solution. Aspartic acid, serine, lysine, glycine, and tyrosine were used as starting materials for the diketopiperazines. Aromatic and aliphatic comonomers were used. Thus, we demonstrate the technical feasibility of producing strong, durable resins from abundant domestic resources. These resins show great potential for high‐performance polymers for use in films, fibers, and composites. © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 78: 2213–2218, 2000

Synthesis and solvent-controlled self-assembly of diketopiperazine-based polyamides from aspartame

“…In addition, the rigid structure of DKP may impart high thermal and mechanical properties to polymeric materials. 20,21 The continuous hydrogen bonding of DKP units in polymer chains may lead to unique selfassembly. 22 However, only a few DKP-based polymers have been reported, and their self-assembly properties have not been adequately studied.…”

“…22 However, only a few DKP-based polymers have been reported, and their self-assembly properties have not been adequately studied. [20][21][22][23][24] The main problem in the development of DKP-based polymers is the low solubility, which induces lower molecular weight and complicates property evaluation. Thus, the design of DKP monomers with high solubility is important for obtaining self-assembled DKP polymers.…”

The Structural Characterisation and DFT-Aided Interpretation of Vibrational Spectra for Cyclo(l-Cys-d-Cys) Cyclic Dipeptide in a Solid State

“…In addition, their native ability to bind to a wide range of receptors makes them promising templates for drug development [6,7]. Diverse biological properties of 2,5-diketopiperazine-based cyclic dipeptides include antitumor [8], antimicrobial [9], and neuroprotective activity [10], while in chemical applications, they are used as catalysts [11], building blocks for self-assembling hydrogels [12], and polymers with high melting point [13], among others, as reviewed in [14][15][16][17][18].…”

Syntheses and Characterizations of Cysteine-Derived Compounds and Polymers

“…The history of incorporating DKP in polymer preparation could be traced back to 1968 and now, the synthesis of DKP containing polymer is well developed. 118 A series of DKP-based polymers have been successfully produced such as aspartic DKP-containing polyesters, serine DKP-containing polyesters, lysine DKP-containing polyamides and lysine DKP-containing polyurethanes (Fig.1.14) 118,119. It was reported that the DKP-containing polymers possessed good thermal and mechanical properties.…”