Enantioselectivity on Surfaces with Chiral Nanostructures

Rampulla, David M.; Gellman, Andrew J.

doi:10.1201/9781439834398.ch73

Cited by 4 publications

(6 citation statements)

References 54 publications

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“…To study the properties of chiral molecular structures on surfaces, simple molecules are needed. A significant effort has gone into investigating small amino acids on surfaces as they are building blocks for peptides, proteins, and manufactured drugs. − …”

Section: Introductionmentioning

confidence: 99%

“…Cysteine, a small amino acid with a thiol side chain, is an ideal test bed for the study of small molecule adsorption properties in a chiral environment. Chiral metal surfaces are inherently chiral interfaces produced by cleaving the crystal at a particular angle to generate a set of miller indices that are non-zero and all different, such as {531}, or {643}, or even {1 5 17}. − These surfaces are nonsymmetric because of the formation of step kinks as shown by the circled top layer atoms in Figure . The chirality of these kinks is determined by the clockwise or anticlockwise combination of low index microfacets that make up the kink site. , Just like chiral molecules, the handedness of the surface is denoted by R and S or D and L, for example, Cu{531} R .…”

Section: Introductionmentioning

confidence: 99%

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Enantiospecific Adsorption and Decomposition of Cysteine Enantiomers on the Chiral Cu{421}^R Surface

et al. 2019

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A detailed understanding of the bonding and molecular geometry characteristics of amino acids on chiral surfaces is vital toward discovering new pathways in chiral chemistry. Saturated layers of d- and l-cysteine amino acids were chemisorbed onto a chiral Cu{421}R surface. Although very little difference was observed in the molecular orientation of the two enantiomers as observed with near-edge X-ray absorption fine structure, a large variation in the sulfur bond scission energy was measured using a high-resolution X-ray photoelectron spectroscopy thermal annealing sequence. As a result of this scission process, enantiomers of cysteine molecules completely dissociate into alaninate at temperatures separated by as much as 16 K or 0.06 eV which is one of the largest stereo effects observed on chiral metal surfaces.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enantiospecific Adsorption and Decomposition of Cysteine Enantiomers on the Chiral Cu{421}^R Surface

et al. 2019

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“…28 Generally chiral surfaces can provide an effective environment for chiral molecular discrimination. In the past decade, chiral surfaces 29 have received attention for their potential applications, 1,[30][31][32] such as stereoselective chemi-cal synthesis, separation of chiral compounds, crystal growth, protein adsorption, and optical activity.…”

Section: Introductionmentioning

confidence: 99%

Chiral crystallization of glutamic acid on self assembled films of cysteine

Dressler

Mastai

2007

Chirality

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In this article, we describe the preparation and use of chiral surfaces derived from enantiomerically pure crystals of amino acids. For this purpose, we chose to employ a self-assembly process to grow nanoscale chiral films of (+)-L or (-)-D cysteine, onto gold surfaces. We utilized those chiral films as resolving auxiliaries in the crystallization of enantiomers from solutions. To demonstrate the chiral discriminating ability of the chiral surfaces in crystallization processes, we investigated the crystallization of rac-glutamic acid onto the chiral films. Our study demonstrates the potential application of chiral films to control chirality throughout crystallization, where one enantiomer crystallizes on the chiral surfaces with relatively high enantiomeric excess. In addition, crystallization of pure glutamic acid enantiomers, and its racemic compound on to chiral films resulted in crystal morphology modification with preferred crystal orientation, which assists in the interpretation of the ability of our chiral surfaces to function as chiral selectors.

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“…6,7 Surfaces can be considered chiral if they are based on chiral crystals or on templates with chiral molecules. 8 Hanein et al have examined the interaction of epithelial cells with chiral crystals, and showed that cells attach in a different manner to the two crystal enantiomer surfaces, thus demonstrating sensitivity to surface chirality on the angstrom scale. 9 They reported differential adhesion of epithelial cells to enantiomorphous crystal surfaces of the [011] faces of the (R,R)-and (S,S)-calcium tartrate tetrahydrate.…”

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confidence: 99%

Neuronal Growth on l- and d-Cysteine Self-Assembled Monolayers Reveals Neuronal Chiral Sensitivity

Baranes

Moshe

Alon

et al. 2014

ACS Chem. Neurosci.

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Studying the interaction between neuronal cells and chiral molecules is fundamental for the design of novel biomaterials and drugs. Chirality influences all biological processes that involve intermolecular interaction. One common method used to study cellular interactions with different enantiomeric targets is the use of chiral surfaces. Based on previous studies that demonstrated the importance of cysteine in the nervous system, we studied the effect of L-and D-cysteine on single neuronal growth. L-Cysteine, which normally functions as a neuromodulator or a neuroprotective antioxidant, causes damage at elevated levels, which may occur post trauma. In this study, we grew adult neurons in culture enriched with L-and D-cysteine as free compounds or as self-assembled monolayers of chiral surfaces and examined the effect on the neuronal morphology and adhesion. Notably, we have found that exposure to the L-cysteine enantiomer inhibited, and even prevented, neuronal attachment more severely than exposure to the D-cysteine enantiomer. Atop the L-cysteine surfaces, neuronal growth was reduced and degenerated. Since the cysteine molecules were attached to the surface via the thiol groups, the neuronal membrane was exposed to the molecular chiral site. Thus, our results have demonstrated high neuronal chiral sensitivity, revealing chiral surfaces as indirect regulators of neuronal cells and providing a reference for studying chiral drugs.

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Enantioselectivity on Surfaces with Chiral Nanostructures

Cited by 4 publications

References 54 publications

Enantiospecific Adsorption and Decomposition of Cysteine Enantiomers on the Chiral Cu{421}^R Surface

Enantiospecific Adsorption and Decomposition of Cysteine Enantiomers on the Chiral Cu{421}^R Surface

Chiral crystallization of glutamic acid on self assembled films of cysteine

Neuronal Growth on l- and d-Cysteine Self-Assembled Monolayers Reveals Neuronal Chiral Sensitivity

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Enantioselectivity on Surfaces with Chiral Nanostructures

Cited by 4 publications

References 54 publications

Enantiospecific Adsorption and Decomposition of Cysteine Enantiomers on the Chiral Cu{421}R Surface

Enantiospecific Adsorption and Decomposition of Cysteine Enantiomers on the Chiral Cu{421}R Surface

Chiral crystallization of glutamic acid on self assembled films of cysteine

Neuronal Growth on l- and d-Cysteine Self-Assembled Monolayers Reveals Neuronal Chiral Sensitivity

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Product

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Enantiospecific Adsorption and Decomposition of Cysteine Enantiomers on the Chiral Cu{421}^R Surface

Enantiospecific Adsorption and Decomposition of Cysteine Enantiomers on the Chiral Cu{421}^R Surface