Abstract
One enantiomer of an initially racemic mixture of α-amino acids can be preferentially removed from solution by selective incorporation into the opposite enantiotopic faces of growing centrosymmetric crystals of the α-form of glycine1,16. We report here that oriented growth of crystals of the α form of glycine has been achieved under chiral Langmuir monolayers comprising amphiphilic α-amino acids, by virtue of a structural match between the monolayer and the ac surface layer of the attached growing glycine crystals. Such monolayers of α-amino acid of R configuration, containing long hydrocarbon chains, induce glycine to crystallize with its (010) face attached to the monolayer, and by symmetry the corresponding S amino-acid monolayers induce attachment of the (0&1macr;0) face of glycine. Replacement of the hydrocarbon by a fluorocarbon chain induces analogous crystallizations, albeit, with only a partial degree of orientation, whereas monolayers of a resolved amino acid bearing a cholestanoyl moiety do not promote crystallization of glycine. Monolayers of the R, S-amino acids induce attachment of both (010) and (0&1macr;0) faces of glycine. These results on oriented crystal growth provide a new route for efficient amplification of optical activity of amino acids present in solution, through the enantioselective occlusion into the growing crystals of glycine1 at water–air interfaces covered by a monolayer.
This is a preview of subscription content, access via your institution
Access options
Subscribe to this journal
Receive 51 print issues and online access
$199.00 per year
only $3.90 per issue
Buy this article
- Purchase on Springer Link
- Instant access to full article PDF
Prices may be subject to local taxes which are calculated during checkout
Similar content being viewed by others
References
Weissbuch, I. et al. Nature 310, 161–164 (1984).
Legros, J. P. & Kvick, A. Acta crystallogr. B36, 3052–3059 (1980).
Arsentiev, V. A. & Leja, J. in Colloid and Interface Science Vol. 5 (ed. Kerker, M.) 251–270 (Academic, New York, 1976).
Barnes, G. T. in Colloid Science Vol. 2 (ed. Everett, D. H.) 173–190 (Chemical Society, London, 1975).
Arrington, C. H. Jr., & Patterson, G. D. J. phys. Chem. 57, 247–250 (1953).
Bernett, M. K. & Zisman, W. A. J. phys. Chem. 67, 1534–1540 (1963).
Stewart, M. V. & Arnett, E. M. Topics Stereochem. 13, 195–262 (1982).
Seul, M., Eisenberger, P. & McConnell, H. M. Proc. natn. Acad. Sci. U.S.A. 80, 5795–5797 (1983).
Als-Nielsen, J. & Pershan, P. S. Nucl. instrum. Meth. 208, 545–548 (1983).
Weissbuch, I. et al. J. Am. chem. Soc. 105, 6615–6621 (1983).
Maoz, R. & Sagiv, J. J. Colloid Interface Sci. 100, 465–496 (1984).
Netzer, L., Iscovici, R. & Sagiv, J. Thin Solid Films 99, 235–241 (1983); 100, 67ndash;76 (1983).
Koenig, W. A., Benecke, I. & Sievers, S. J. Chromat. 217, 71–79 (1981).
Fromherz, P. Rev. scient. Instrum. 46, 1380–1385 (1975).
Weinstein, S. Angew. Chem. 21, 218 (1982).
Addadi, L. et al. Angew. Chem. int. Ed. 24, 466–485 (1985).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Landau, E., Levanon, M., Leiserowitz, L. et al. Transfer of structural information from Langmuir monolayers to three-dimensional growing crystals. Nature 318, 353–356 (1985). https://doi.org/10.1038/318353a0
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1038/318353a0
This article is cited by
-
Control of crystal nucleation by patterned self-assembled monolayers
Nature (1999)
-
Controlling local disorder in self-assembled monolayers by patterning the topography of their metallic supports
Nature (1998)
-
An ultrastructural study of the effects of acidic phospholipid substitutions on calcium phosphate precipitation in anionic liposomes
Calcified Tissue International (1992)
-
Crystallization of an inorganic phase controlled by a polymer matrix
Nature (1991)
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.