Using fast scanning calorimetry to study solid-state cyclization of dipeptide L-leucyl-L-leucine

Safiullina, Aisylu S.; Buzyurov, Aleksey V.; Ziganshina, S. A.; Gerasimov, Alexander V.; Schick, Christoph; Gorbatchuk, Valery V.; Зиганшин, Марат А.

doi:10.1016/j.tca.2020.178748

Cited by 16 publications

(6 citation statements)

References 59 publications

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“…Since the first reports, , it has been generally recognized through mass spectrometry techniques that the sublimation of linear dipeptides may lead to the cyclization of the compound. This thermally induced cyclization has been confirmed by further reports, − and it is mentioned also in more recent studies. , However, a clear understanding of the process, combining measurements and computational studies, is still lacking, mainly due to the competition between thermal decomposition and cyclization reactions, − with the former often dominating.…”

Section: Introductionsupporting

confidence: 60%

Insights into the Thermally Activated Cyclization Mechanism in a Linear Phenylalanine-Alanine Dipeptide

et al. 2022

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Dipeptides, the prototype peptides, exist in both linear ( l -) and cyclo ( c -) structures. Since the first mass spectrometry experiments, it has been observed that some l -structures may turn into the cyclo ones, likely via a temperature-induced process. In this work, combining several different experimental techniques (mass spectrometry, infrared and Raman spectroscopy, and thermogravimetric analysis) with tight-binding and ab initio simulations, we provide evidence that, in the case of l -phenylalanyl- l -alanine, an irreversible cyclization mechanism, catalyzed by water and driven by temperature, occurs in the condensed phase. This process can be considered as a very efficient strategy to improve dipeptide stability by turning the comparatively fragile linear structure into the robust and more stable cyclic one. This mechanism may have played a role in prebiotic chemistry and can be further exploited in the preparation of nanomaterials and drugs.

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Section: Introductionsupporting

confidence: 60%

Insights into the Thermally Activated Cyclization Mechanism in a Linear Phenylalanine-Alanine Dipeptide

et al. 2022

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“…The molar heat capacity C p,m of dry γ-cyclodextrin was measured using Netzsch DSC204 F1 Phoenix differential scanning calorimeter. This procedure using sapphire disk as a standard sample was described in detail earlier [ 12 ].…”

Section: Methodsmentioning

confidence: 99%

“…A state-of-the-art method for determination of melting parameters for compounds of low thermal stability is fast scanning calorimetry (FSC) [ 6 , 11 , 12 , 13 ]. FSC was used to determine melting properties of thermally labile biomolecules: proteins [ 14 ], peptides [ 15 ], amino acids [ 5 ], pharmaceuticals [ 16 , 17 ], mono and disaccharides [ 1 ], and nucleobases [ 18 ].…”

Section: Introductionmentioning

confidence: 99%

Determination of Melting Parameters of Cyclodextrins Using Fast Scanning Calorimetry

Gatiatulin

Grishin

Buzyurov

et al. 2022

IJMS

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The first evidence of native cyclodextrins fusion was registered using fast scanning calorimetry (FSC) with heating rates up to 40,000 K s−1. The endothermal effects, detected at low heating rates, correspond to the decomposition processes. Upon the increase of the heating rate the onset of these effects shifts to higher temperatures, reaching a limiting value at high heating rates. The limiting temperatures were identified as the melting points of α-, β- and γ-cyclodextrins, as the decomposition processes are suppressed at high heating rates. For γ-cyclodextrin the fusion enthalpy was measured. The activation energies of thermal decomposition of cyclodextrins were determined by dependence of the observed thermal effects on heating rates from 4 K min−1 in conventional differential scanning calorimetry to 40,000 K s−1 in FSC. The lower thermal stability and activation energy of decomposition of β-cyclodextrin than for the other two cyclodextrins were found, which may be explained by preliminary phase transition and chemical reaction without mass loss. The obtained values of fusion parameters of cyclodextrins are needed in theoretical models widely used for prediction of solubility and solution rates and in preparation of cyclodextrin inclusion compounds involving heating.

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“…CDPs can be synthesized also in the solid state, through the heating of a powder sample [ 88 , 89 ]. The appropriate reaction temperature depends on the nature of the peptide sequence.…”

Section: Synthesis Of Cdpsmentioning

confidence: 99%

Diketopiperazine Gels: New Horizons from the Self-Assembly of Cyclic Dipeptides

Scarel

Marchesan

2021

Molecules

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Cyclodipeptides (CDPs) or 2,5-diketopiperazines (DKPs) can exert a variety of biological activities and display pronounced resistance against enzymatic hydrolysis as well as a propensity towards self-assembly into gels, relative to the linear-dipeptide counterparts. They have attracted great interest in a variety of fields spanning from functional materials to drug discovery. This concise review will analyze the latest advancements in their synthesis, self-assembly into gels, and their more innovative applications.

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Using fast scanning calorimetry to study solid-state cyclization of dipeptide L-leucyl-L-leucine

Cited by 16 publications

References 59 publications

Insights into the Thermally Activated Cyclization Mechanism in a Linear Phenylalanine-Alanine Dipeptide

Insights into the Thermally Activated Cyclization Mechanism in a Linear Phenylalanine-Alanine Dipeptide

Determination of Melting Parameters of Cyclodextrins Using Fast Scanning Calorimetry

Diketopiperazine Gels: New Horizons from the Self-Assembly of Cyclic Dipeptides

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