Enantioselective Adsorption of Phenylalanine onto Self-Assembled Monolayers of 1,1‘-Binaphthalene-2,2‘-dithiol on Gold

Nakanishi, Tetsuya; Yamakawa, Naoko; Asahi, Toru; Osaka, Tetsuya; Ohtani, Bunsho; Uosaki, Kohei

doi:10.1021/ja012084x

Cited by 46 publications

(30 citation statements)

References 11 publications

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“…The adsorption energies for (R)-L and (S)-D complexes by HF/6-31G** are larger than those for (R)-D and (S)-L, which agree well with the experimental results [9]. Also, the order of BSSE-corrected HF energies for (R)-D and (R)-L complexes is unchanged.…”

Section: Ab Initio Calculation Of Adsorption Energiessupporting

confidence: 87%

“…1 (a, b), is produced by covalent-bond formation between the sulfur atom in BNSH and the surface gold atom and plausibly by CH-π interaction between adjacent naphthalene groups. When the (R)-or (S)-BNSH-modified gold was immersed in aqueous solutions of an enantiomer of either phenylalanine (Phe) [9] or thalidomide [10], the TDC surface adsorbed only one enantiomer of the chiral molecule.…”

Section: Introductionmentioning

confidence: 99%

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Origin of chiral discrimination by a two-dimensionally chiral self-assembled monolayer: A quantum chemical study

Nishikawa

Torimoto

Nakanishi

et al. 2006

Chemical Physics Letters

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Section: Ab Initio Calculation Of Adsorption Energiessupporting

confidence: 87%

Section: Introductionmentioning

confidence: 99%

Origin of chiral discrimination by a two-dimensionally chiral self-assembled monolayer: A quantum chemical study

Nishikawa

Torimoto

Nakanishi

et al. 2006

Chemical Physics Letters

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“…19 An increasingly important class of metal surfaces are those modified with a chiral molecule, [20][21] which have for example been used for heterogeneous enantioselective catalysis 22 and chiral discrimination. [23][24] The discrimination between and separation of enantiomers or the selective production of one enantiomer is of great importance, as chirality is a fundamental aspect of molecular biology. The structure of the adsorbed molecules plays a fundamental role in these processes.…”

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confidence: 99%

Vibrational circular dichroism of N-acetyl-l-cysteine protected gold nanoparticles

Gautier

Bürgi

2005

Chem. Commun.

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Vibrational circular dichroism is used to determine the conformation of a thiol adsorbed on gold nanoparticles.Monolayer protected metal nanoparticles are of considerable interest due to their potential application in various fields such as bio-sensing, catalysis, electronics and nanotechnology.1 Whereas the physical properties of monolayer protected nanoparticles (MPNs) are largely associated with the metal core, their chemical behaviour such as solubility, molecular recognition and organization, is determined by the protection layer. The engineering of the latter is currently making tremendous progress. 2 The conformation of the molecules adsorbed on the metal particles directly affects the chemical properties. Structure determination would therefore greatly help the rational design of functionalized particles. Vibrational circular dichroism (VCD) spectroscopy, i.e. the differential absorption of left and right circular polarized infrared light, yields detailed information on the conformation of a chiral molecule in solution.3 VCD is more sensitive towards conformation than infrared (IR) spectroscopy and its power for structure determination of dissolved molecules, by the comparison between experimental and theoretical spectra, has impressively been demonstrated in the past. 4-7In this contribution we show that very small (,2 nm) gold nanoparticles chirally modified with N-acetyl-L-cysteine (Scheme 1) exhibit VCD activity associated with the molecules in the protection layer. Comparison with calculated VCD spectra of N-acetyl-L-cysteine adsorbed on small gold clusters allows getting rather detailed structural information. Whereas optical activity in the UV-vis of MPNs has been reported before, 8 to the best of our knowledge this is the first report on the VCD activity associated with MPNs.

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“…Recently, several kinds of SAMs consisting of chiral molecules were reported to show enantioselectivity. [3][4][5][6][7][8] In the present study, we focused our attention on the chiral amino acid, cysteine (Cys), because Cys is known to form a SAM on gold, [9][10][11][12][13][14] and it is a building block of proteins playing an important role in several enantioselective physiological processes. Here, the number of Cys molecules adsorbed on a unit area of gold surface, or the surface coverage of Cys monolayer on the gold surface, is known to be affected by the conditions under which the SAM is prepared, such as immersion time in the solution, solvent used for preparing the solution, and surface condition of the substrate.…”

Section: Introductionmentioning

confidence: 99%

Effect of surface coverage of gold(111) electrode with cysteine on the chiral discrimination of DOPA

et al. 2007

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The enantioselectivity imparted to a gold electrode by modifying its surface with a self-assembled monolayer (SAM) of cysteine (Cys) was investigated for the electrochemical redox reaction of 3,4-dihydroxyphenylalanine (DOPA). A cyclic voltammetric study of the redox reaction revealed that the enantioselectivity was determined by the surface coverage of the gold electrode with Cys molecules. The electrode modified with approximately 1.8 x 10(14) Cys molecules cm(-2) exhibited enantioselectivity in the voltammogram for the oxidation and reduction of DOPA, while the voltammograms obtained by the electrodes with either more or less surface coverages did not exhibit significant enantioselectivity. It is suggested that the accessibility of DOPA to that area of the gold surface which is not blocked by Cys molecules at an optimum surface coverage, is required for the enantioselective redox reaction of DOPA to proceed.

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Enantioselective Adsorption of Phenylalanine onto Self-Assembled Monolayers of 1,1‘-Binaphthalene-2,2‘-dithiol on Gold

Cited by 46 publications

References 11 publications

Origin of chiral discrimination by a two-dimensionally chiral self-assembled monolayer: A quantum chemical study

Origin of chiral discrimination by a two-dimensionally chiral self-assembled monolayer: A quantum chemical study

Vibrational circular dichroism of N-acetyl-l-cysteine protected gold nanoparticles

Effect of surface coverage of gold(111) electrode with cysteine on the chiral discrimination of DOPA

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