[80]Fullerene–amino acid interactions: Theoretical insights

León, Aned de; Jalbout, Abraham F.; Basiuk, Vladimir A.

doi:10.1002/qua.21780

Cited by 14 publications

(19 citation statements)

References 31 publications

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“…It results that all the 20 aa form favorable complexes with C 60 , with the Leu, Arg, Trp and Glu units featuring the highest calculated binding Fig. This has been further demonstrated when the adsorption of aa on C 80 was modeled with the same computational approach, 73 demonstrating the formation of significantly stronger complexes compared to those formed with C 60 . For each aa the common nomenclature, the full name, the three letters and the one-letter abbreviations are reported.…”

Section: Fullerenes and Amino Acidsmentioning

confidence: 67%

Interfacing proteins with graphitic nanomaterials: from spontaneous attraction to tailored assemblies

2015

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This critical review aims at giving insights on the spontaneous tendency of proteins and their constitutive parts to adsorb on graphitic nanomaterials (GNMs) through non-covalent interactions occurring at their interfaces. Specifically, it focuses on the theoretical and experimental studies carried out to comprehend in depth the forces ruling the adsorption processes of proteins on fullerene, carbon nanotubes and graphene. In a systematic way the reader is guided through the most recent and representative examples describing at the atomistic level of detail the structural modalities and the chemico-physical principles through which amino acids, polypeptides and folded proteins interact with GNMs' surface, thereby taking into consideration the mutual effects of both protein structural complexity and nanomaterial topology. Based on their chemical and structural features, the study and understanding of the protein-nanomaterial interfaces can be exploited in the view of design and control the spontaneous formation of biologically-active hybrid materials for the development of new tailored applications in the field of sensing, nanomedicine and biochemistry.

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Section: Fullerenes and Amino Acidsmentioning

confidence: 67%

Interfacing proteins with graphitic nanomaterials: from spontaneous attraction to tailored assemblies

2015

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“…Table I shows that the ⌬R value is 0.15-Å (compared with that of 0.22-Å in the Ca@ANT system) with a HOMO/LUMO gap of 3.11 kcal/mol (compared with 2.66 kcal/mol in the Ca@ANT molecule). Previous reports [18,24] suggest that Ca prefers to localize along the center of the molecular system under consideration. Typically in fullerenes this is the case, but since the SWNT considered is capped the behavior may in fact be consistent.…”

Section: Group 1: Amino Acids With Aliphatic R-groupsmentioning

confidence: 99%

“…The reactivity of amino acids, for example, with SWNT species is directly related to several properties. In our group we have investigated the stability of amino acids with fullerenes [17], lithium encapsulated in fullerenes (or Li@C 60 ) [18], and the armchair (5,5) SWNT [19]. Such calculations reveal favorable interaction energies with the amino acids.…”

Section: Introductionmentioning

confidence: 99%

“…This is interesting as it shows that the valence charge density of the metal will be transferred to specific sites of the SWNT or fullerene. This effect has been shown of course to increase the affinity of fullerenes to amino acids [18]. Recent reports on the interaction of glycine on an armchair (3,3) surface show that stable complexes can form on the surface of graphene and SWNT sheets [25].…”

Section: Introductionmentioning

confidence: 99%

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Endo[metallo] SWNT‐amino acid interactions: A theoretical study

Jalbout

2009

Int J of Quantum Chemistry

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ABSTRACT:We propose that an atom of calcium (Ca) which is an alkaline earth metal on encapsulation inside of a metallic armchair (5,5) (SWNT) species can have stronger amino acid interactions. From our calculations of various physical parameters we depict several configurations in which such an endo[metallo] SWNT can be modified by an internally placed Ca atom. Density functional theory (DFT) calculations reveal that the most favorable interactions of the SWNT system is with tryptophan, tyrosine, and phenylalanine that can be directly correlated to the backbone geometry of the amino acid species.

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“…Carbon nanotubes and fullerenes are known to form relatively strong non-covalent interactions with a wide range of amines 22 and amino acids, [23][24][25][26][27] including proline. [28][29][30][31] Whilst the nature of interactions between proline and carbon nanostructures is still not definitively understood, the exact mechanism is likely to reflect a number of cooperative forces, including ionic interactions, 32 N-H … π hydrogen bonding interactions 33 and electron transfer interactions. 34,35 Of these, the back-donation of the lone pair electrons from the occupied N non-bonding orbital on proline to the vacant C=C π* antibonding orbitals of the carbon nanotube appears to be the most important factor for controlling the proline-nanotube interaction (Fig.…”

Section: Introductionmentioning

confidence: 99%

The effects of interactions between proline and carbon nanostructures on organocatalysis in the Hajos–Parrish–Eder–Sauer–Wiechert reaction

Rance

Khlobystov

2014

Nanoscale

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A note on versions:The version presented here may differ from the published version or from the version of record. If you wish to cite this item you are advised to consult the publisher's version. Please see the repository url above for details on accessing the published version and note that access may require a subscription. The non-covalent interactions of S-(-)-proline with the surfaces of carbon nanostructures (fullerene, nanotubes and graphite) change the nucleophilic-electrophilic and acid-base properties of the amino acid, thus tuning its activity and selectivity in the organocatalytic HajosParrish-Eder-Sauer-Wiechert (HPESW) reaction. Whilst our spectroscopy and microscopy measurements show no permanent covalent bonding between S-(-)-proline and carbon nanostructures, a systematic investigation of the catalytic activity and selectivity of the organocatalyst in the HPESW reaction demonstrates a clear correlation between the pyramidalisation angle of carbon nanostructures and the catalytic properties of S-(-)-proline. Carbon nanostructures with larger pyramidalisation angles have a stronger interaction wit h the nitrogen atom lone pair of electrons of the organocatalyst, thereby simultaneously decreasing the nucleophilicity and increasing the acidity of the organocatalyst. These translate into lower conversion rates but higher selectivities towards the dehydrated product of Aldol addition.

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[80]Fullerene–amino acid interactions: Theoretical insights

Cited by 14 publications

References 31 publications

Interfacing proteins with graphitic nanomaterials: from spontaneous attraction to tailored assemblies

Interfacing proteins with graphitic nanomaterials: from spontaneous attraction to tailored assemblies

Endo[metallo] SWNT‐amino acid interactions: A theoretical study

The effects of interactions between proline and carbon nanostructures on organocatalysis in the Hajos–Parrish–Eder–Sauer–Wiechert reaction

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