Vibrational and conformational studies of 1,3-diaminopropane and its N-deuterated and N-ionised derivatives

Mendes, Sofia R. O.; Amado, Ana M.; Tomkinson, J.; Marques, M. P. M.; Carvalho, Luís A. E. Batista de

doi:10.1039/c7nj00810d

Cited by 8 publications

(2 citation statements)

References 51 publications

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“…A mismatch between observed and calculated –NH 3 + torsional energies is commonly found, e.g. for aliphatic amines 36 and aromatic hydrochlorides 32 .…”

Section: Resultsmentioning

confidence: 99%

Structure and spectroscopy of methionyl-methionine for aquaculture

Parker

Funnell

Shankland

et al. 2021

Sci Rep

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The amino acid l-methionine is an essential amino acid and is commonly used as a feed supplement in terrestrial animals. It is less suitable for marine organisms because it is readily excreted. It is also highly water soluble and this results in loss of the feed and eutrophication of the water. To address these problems, the dipeptide dl-methionyl-dl-methionine (trade name: AQUAVI Met-Met) has been developed as a dedicated methionine source for aquaculture. The commercial product is a mixture of a racemic crystal form of d-methionyl-d-methionine/l-methionyl-l-methionine and a racemic crystal form of d-methionyl-l-methionine/l-methionyl-d-methionine. In this work, we have computationally, structurally, spectroscopically and by electron microscopy characterised these materials. The microscopy and spectroscopy demonstrate that there is no interaction between the dd–ll and dl–ld racemates on any length scale from the macroscopic to the nanoscale.

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“…A mismatch between observed and calculated –NH 3 + torsional energies is commonly found, e.g. for aliphatic amines 36 and aromatic hydrochlorides 32 .…”

Section: Resultsmentioning

confidence: 99%

Structure and spectroscopy of methionyl-methionine for aquaculture

Parker

Funnell

Shankland

et al. 2021

Sci Rep

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“…Initially, the electronic structure, optimized geometries, vibrational frequencies, natural bond orbital (NBO) analysis, and molecular electrostatic potential surface (MEPS) of EZT, L -proline, and EZT- L -proline cocrystals were calculated by using density functional theory with B3LYP ( Lee et al, 1988 ; Becke, 1993 ; Parr and Yang, 1995 ; Shukla et al, 2017 ) functional employing 6–311++G(d,p) basis set ( Petersson et al, 1988 ; Petersson and Al-Laham, 1991 ; Chai and Head-Gordon, 2008 ; Mendes et al, 2017 ). All calculations were done with the Gaussian 09 package program ( Frisch et al, 2009 ).…”

Section: Computational Detailsmentioning

confidence: 99%

Molecular Structural, Hydrogen Bonding Interactions, and Chemical Reactivity Studies of Ezetimibe-L-Proline Cocrystal Using Spectroscopic and Quantum Chemical Approach

et al. 2022

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Ezetimibe (EZT) being an anticholesterol drug is frequently used for the reduction of elevated blood cholesterol levels. With the purpose of improving the physicochemical properties of EZT, in the present study, cocrystals of ezetimibe with L-proline have been studied. Theoretical geometry optimization of EZT-L-proline cocrystal, energies, and structure–activity relationship was carried out at the DFT level of theory using B3LYP functional complemented by 6-311++G(d,p) basis set. To better understand the role of hydrogen bonding, two different models (EZT + L-proline and EZT + 2L-proline) of EZT-L-proline cocrystal were studied. Spectral techniques (FTIR and FT-Raman) combined with quantum chemical methodologies were successfully implemented for the detailed vibrational assignment of fundamental modes. It is a zwitterionic cocrystal hydrogen bonded with the OH group of EZT and the COO− group of L-proline. The existence and strength of hydrogen bonds were examined by a natural bond orbital analysis (NBO) supported by the quantum theory of atoms in molecule (QTAIM). Chemical reactivity was reflected by the HOMO–LUMO analysis. A smaller energy gap in the cocrystal in comparison to API shows that a cocrystal is softer and chemically more reactive. MEPS and Fukui functions revealed the reactive sites of cocrystals. The calculated binding energy of the cocrystal from counterpoise method was −11.44 kcal/mol (EZT + L-proline) and −26.19 kcal/mol (EZT + 2L-proline). The comparative study between EZT-L-proline and EZT suggest that cocrystals can be better used as an alternative to comprehend the effect of hydrogen bonding in biomolecules and enhance the pharmacological properties of active pharmaceutical ingredients (APIs).

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Physical-chemical studies on putrescine (butane-1,4-diamine) and its solutions: Experimental and computational investigations

Campetella

Cappelluti

Fasolato

et al. 2021

Journal of Molecular Liquids

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Vibrational and conformational studies of 1,3-diaminopropane and its N-deuterated and N-ionised derivatives

Abstract: A scarce understanding of the biological role of 1,3-diaminopropane highlights the relevance of attaining its full conformational preferences, using combined FTIR, Raman and INS spectroscopies.

Cited by 8 publications

References 51 publications

Structure and spectroscopy of methionyl-methionine for aquaculture

Structure and spectroscopy of methionyl-methionine for aquaculture

Molecular Structural, Hydrogen Bonding Interactions, and Chemical Reactivity Studies of Ezetimibe-L-Proline Cocrystal Using Spectroscopic and Quantum Chemical Approach

Physical-chemical studies on putrescine (butane-1,4-diamine) and its solutions: Experimental and computational investigations

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