Molecular Self‐Assembly of Cyclic Dipeptide Derivatives and Their Applications

Manchineella, Shivaprasad; Govindaraju, T.

doi:10.1002/cplu.201600450

Cited by 106 publications

(113 citation statements)

References 118 publications

(127 reference statements)

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“…[19][20][21][22][23][24][25][26] Peptide sequences as short as two or three amino acids have been utilized for nanostructure formation in a sequence dependent manner using linear [27][28][29][30][31][32] or cyclic peptides. [33][34][35][36] Cyclic dipeptides (or diketopiperazines) involve the presentation of amino acid side chain functionality at the exterior of the nanostructure, thus rendering it accessible for interactions and/ or functionalization. Govindaraju's group has extensively investigated their assembly, highlighting interesting properties of these systems, including the increased stability towards proteolysis.…”

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confidence: 99%

Spontaneous Aminolytic Cyclization and Self‐Assembly of Dipeptide Methyl Esters in Water

et al. 2020

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Dipeptides are known to spontaneously cyclize to diketopiperazines, and in some cases these cyclic dipeptides have been shown to self‐assemble to form supramolecular nanostructures. Herein, we demonstrate the in situ cyclization of dipeptide methyl esters in aqueous buffer by intramolecular aminolysis, leading to the formation of diverse supramolecular nanostructures. The chemical nature of the amino acid side chains dictates the supramolecular arrangement and resulting nanoscale architectures. For c[LF], supramolecular gels are formed, and the concentration of starting materials influences the mechanical properties of these hydrogels. Moreover, by adding metalloporphyrins to the starting dipeptide starting solution, these become incorporated through cooperative assembly, resulting in the formation of nanofibers able to catalyse the oxidation of organic phenol in water. The approach taken here, which combines chemically activated assembly with the versatility of short peptides, demonstrates a new and easy method to achieving spontaneous formation of a variety of functional supramolecular materials using simple building blocks.

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confidence: 99%

Spontaneous Aminolytic Cyclization and Self‐Assembly of Dipeptide Methyl Esters in Water

et al. 2020

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“…They are attractive scaffolds for drug discoveries and their modifications have been recently the subject of intense research leading to attractive molecules for medical, catalysis, or self-assembly applications. 12,13 Nevertheless, DKPs have received little attention in the field of polymer chemistry. 14 To the best of our knowledge, only two examples of polymer N-grafted DKP have been published.…”

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confidence: 99%

Modification of proline‐based 2,5‐diketopiperazines by anionic ring‐opening polymerization

Tezgel

Puchelle

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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2,5-Diketopiperazines (DKPs) are the smallest cyclic dipeptides found in nature with various attractive properties. In this study, we have demonstrated the successful modification of proline-based DKPs using anionic ring-opening polymerization (AROP) as a direct approach. Four different proline-based DKPs with various side chains and increasing steric hindrance were used as initiating species for the polymerization of 1,2-epoxybutane or ethoxyethyl glycidyl ether in the presence of t-BuP 4 phosphazene base. The addition of a Lewis acid, tri-isobutyl aluminum, to the reaction mixture strongly decreased the occurrence of side reactions. Impact of the DKP side-chain functionalities on molar mass control and dispersity was successfully evidenced.

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“…Oligopeptides are important building blocks for the synthesis of supramolecular structures due to their self‐assembly capabilities . The wealth of nanostructures formed opens a wide range of applications in the field of biosensors, organic semiconductors, and drug delivery .…”

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confidence: 99%

Solid‐state synthesis of cyclo LD‐diphenylalanine: A chiral phase built from achiral subunits

2020

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The solid-state structure of LL/DD or LD/DL diphenylalanine diluted in KBr pellets is studied by infrared (IR) absorption and vibrational circular dichroism (VCD) spectroscopy. The structure depends on the absolute configuration of the residues. The natural LL diphenylalanine exists as a mixture of neutral and zwitterionic structures, depending on the humidity of the sample, while mostly the zwitterion is observed for LD diphenylalanine whatever the experimental conditions. The system undergoes spontaneous cyclization upon heating at 125 C, resulting to the formation of a diketopiperazine (DKP) dipeptide as the only product. The reaction is faster for LD than for LL diphenylalanine. As expected, LL and DD diphenylalanine react to form the LL and DD enantiomers of cyclo diphenylalanine. Interestingly, the DKP dipeptides formed from the LD or DL diphenylalanine show unexpected optical activity, with opposite VCD spectra for the products formed from the LD and DL reagents. This is explained in terms of chirality synchronization between the monomers within the crystal, which retain the symmetry of the reagent, resulting to the formation of a new chiral phase made from transiently chiral molecules. K E Y W O R D Schirality synchronization, diketopiperazine (DKP), peptides, vibrational circular dichroism (VCD), vibrational spectroscopy

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Molecular Self‐Assembly of Cyclic Dipeptide Derivatives and Their Applications

Cited by 106 publications

References 118 publications

Spontaneous Aminolytic Cyclization and Self‐Assembly of Dipeptide Methyl Esters in Water

Spontaneous Aminolytic Cyclization and Self‐Assembly of Dipeptide Methyl Esters in Water

Modification of proline‐based 2,5‐diketopiperazines by anionic ring‐opening polymerization

Solid‐state synthesis of cyclo LD‐diphenylalanine: A chiral phase built from achiral subunits

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