Chiral recognition in dimerization of adsorbed cysteine observed by scanning tunnelling microscopy

Kühnle A, Linderoth TR, Hammer B, Besenbacher F (2002)
Nature 415(6874): 891-893.

Download
OA 321.08 KB
Zeitschriftenaufsatz | Veröffentlicht | Englisch
Autor
; ; ;
Abstract / Bemerkung
Stereochemistry plays a central role in controlling molecular recognition and interaction: the chemical and biological properties of molecules depend not only on the nature of their constituent atoms but also on how these atoms are positioned in space. Chiral specificity is consequently fundamental in chemical biology and pharmacology(1,2) and has accordingly been widely studied. Advances in scanning probe microscopies now make it possible to probe chiral phenomena at surfaces at the molecular level. These methods have been used to determine the chirality of adsorbed molecules(3-5), and to provide direct evidence for chiral discrimination in molecular interactions(6) and the spontaneous resolution of adsorbates into extended enantiomerically pure overlayers(3,7-9). Here we report scanning tunnelling microscopy studies of cysteine adsorbed to a (110) gold surface, which show that molecular pairs formed from a racemic mixture of this naturally occurring amino acid are exclusively homochiral, and that their binding to the gold surface is associated with local surface restructuring. Density-functional theory(10) calculations indicate that the chiral specificity of the dimer formation process is driven by the optimization of three bonds on each cysteine molecule. These findings thus provide a clear molecular-level illustration of the well known three-point contact model(11,12) for chiral recognition in a simple bimolecular system.
Erscheinungsjahr
Zeitschriftentitel
Nature
Band
415
Zeitschriftennummer
6874
Seite
891-893
ISSN
PUB-ID

Zitieren

Kühnle A, Linderoth TR, Hammer B, Besenbacher F. Chiral recognition in dimerization of adsorbed cysteine observed by scanning tunnelling microscopy. Nature. 2002;415(6874):891-893.
Kühnle, A., Linderoth, T. R., Hammer, B., & Besenbacher, F. (2002). Chiral recognition in dimerization of adsorbed cysteine observed by scanning tunnelling microscopy. Nature, 415(6874), 891-893. doi:10.1038/415891a
Kühnle, A., Linderoth, T. R., Hammer, B., and Besenbacher, F. (2002). Chiral recognition in dimerization of adsorbed cysteine observed by scanning tunnelling microscopy. Nature 415, 891-893.
Kühnle, A., et al., 2002. Chiral recognition in dimerization of adsorbed cysteine observed by scanning tunnelling microscopy. Nature, 415(6874), p 891-893.
A. Kühnle, et al., “Chiral recognition in dimerization of adsorbed cysteine observed by scanning tunnelling microscopy”, Nature, vol. 415, 2002, pp. 891-893.
Kühnle, A., Linderoth, T.R., Hammer, B., Besenbacher, F.: Chiral recognition in dimerization of adsorbed cysteine observed by scanning tunnelling microscopy. Nature. 415, 891-893 (2002).
Kühnle, Angelika, Linderoth, Trolle R., Hammer, Bjoerk, and Besenbacher, Flemming. “Chiral recognition in dimerization of adsorbed cysteine observed by scanning tunnelling microscopy”. Nature 415.6874 (2002): 891-893.
Alle Dateien verfügbar unter der/den folgenden Lizenz(en):
Copyright Statement:
This Item is protected by copyright and/or related rights. [...]
Volltext(e)
Access Level
OA Open Access
Zuletzt Hochgeladen
2018-08-31T13:12:15Z

122 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Amplification of chirality in two-dimensional enantiomorphous lattices.
Fasel R, Parschau M, Ernst KH., Nature 439(7075), 2006
PMID: 16437111
Scanning tunneling microscopy manipulation of complex organic molecules on solid surfaces.
Otero R, Rosei F, Besenbacher F., Annu Rev Phys Chem 57(), 2006
PMID: 16599819
Chiral switching by spontaneous conformational change in adsorbed organic molecules.
Weigelt S, Busse C, Petersen L, Rauls E, Hammer B, Gothelf KV, Besenbacher F, Linderoth TR., Nat Mater 5(2), 2006
PMID: 16415876
Two-dimensional hierarchical self-assembly of one-handed helical polymers on graphite.
Sakurai S, Okoshi K, Kumaki J, Yashima E., Angew Chem Int Ed Engl 45(8), 2006
PMID: 16411264
Two-dimensional crystals: through the looking glass.
Richardson N., Nat Mater 5(2), 2006
PMID: 16449992
Biomolecular rods and tubes in nanotechnology.
Bittner AM., Naturwissenschaften 92(2), 2005
PMID: 15558225
Evolution of multilevel order in supramolecular assemblies.
Vonau F, Suhr D, Aubel D, Bouteiller L, Reiter G, Simon L., Phys Rev Lett 94(6), 2005
PMID: 15783753
Preparation of chiral surfaces from achiral molecules by controlled symmetry breaking.
Berg AM, Patrick DL., Angew Chem Int Ed Engl 44(12), 2005
PMID: 15712249
Guanine quartet networks stabilized by cooperative hydrogen bonds.
Otero R, Schöck M, Molina LM, Laegsgaard E, Stensgaard I, Hammer B, Besenbacher F., Angew Chem Int Ed Engl 44(15), 2005
PMID: 15761905
Coulombic amino group-metal bonding: adsorption of adenine on Cu110.
Preuss M, Schmidt WG, Bechstedt F., Phys Rev Lett 94(23), 2005
PMID: 16090485
Conservation of chirality in a hierarchical supramolecular self-assembled structure with pentagonal symmetry.
Blüm MC, Cavar E, Pivetta M, Patthey F, Schneider WD., Angew Chem Int Ed Engl 44(33), 2005
PMID: 16037998
Atom-specific identification of adsorbed chiral molecules by photoemission.
Kim JW, Carbone M, Dil JH, Tallarida M, Flammini R, Casaletto MP, Horn K, Piancastelli MN., Phys Rev Lett 95(10), 2005
PMID: 16196965
Adsorption modes of cysteine on Au(111): thiolate, amino-thiolate, disulfide.
Di Felice R, Selloni A., J Chem Phys 120(10), 2004
PMID: 15267352
Circular dichroism in core level photoemission from an adsorbed chiral molecule.
Polcik M, Allegretti F, Sayago DI, Nisbet G, Lamont CL, Woodruff DP., Phys Rev Lett 92(23), 2004
PMID: 15245173
Growth of unidirectional molecular rows of cysteine on Au(110)-(1 x 2) driven by adsorbate-induced surface rearrangements.
Kühnle A, Molina LM, Linderoth TR, Hammer B, Besenbacher F., Phys Rev Lett 93(8), 2004
PMID: 15447200
Nanotechnology and single molecules.
Eggeling C., Chemphyschem 5(10), 2004
PMID: 15535545
Adsorption of thiolates to singly coordinated sites on Au111 evidenced by photoelectron diffraction.
Kondoh H, Iwasaki M, Shimada T, Amemiya K, Yokoyama T, Ohta T, Shimomura M, Kono S., Phys Rev Lett 90(6), 2003
PMID: 12633304
Chemistry: mirrors in flatland.
Raval R., Nature 425(6957), 2003
PMID: 14523427
Enantiospecific electrodeposition of a chiral catalyst.
Switzer JA, Kothari HM, Poizot P, Nakanishi S, Bohannan EW., Nature 425(6957), 2003
PMID: 14523441
Spontaneous resolution under supramolecular control.
Pérez-García L, Amabilino DB., Chem Soc Rev 31(6), 2002
PMID: 12491749

Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®

Quellen

PMID: 11859364
PubMed | Europe PMC

Suchen in

Google Scholar