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Pseudoracemic amino acid complexes: blind predictions for flexible two-component crystals

Pseudoracemic amino acid complexes: blind predictions for flexible two-component crystals
Pseudoracemic amino acid complexes: blind predictions for flexible two-component crystals
Ab initio prediction of the crystal packing in complexes between two flexible molecules is a particularly challenging computational chemistry problem. In this work we present results of single crystal structure determinations as well as theoretical predictions for three 1 ? 1 complexes between hydrophobic L- and D-amino acids (pseudoracemates), known from previous crystallographic work to form structures with one of two alternative hydrogen bonding arrangements. These are accurately reproduced in the theoretical predictions together with a series of patterns that have never been observed experimentally. In this bewildering forest of potential polymorphs, hydrogen bonding arrangements and molecular conformations, the theoretical predictions succeeded, for all three complexes, in finding the correct hydrogen bonding pattern. For two of the complexes, the calculations also reproduce the exact space group and side chain orientations in the best ranked predicted structure. This includes one complex for which the observed crystal packing clearly contradicted previous experience based on experimental data for a substantial number of related amino acid complexes. The results highlight the significant recent advances that have been made in computational methods for crystal structure prediction.



1463-9076
8466-8477
Görbitz, Carl Henrik
bd88808d-a53f-40d1-ba40-43f11edc412f
Dalhus, Bjørn
8d312725-603a-44cf-95dc-b85963bff2fc
Day, Graeme M.
e3be79ba-ad12-4461-b735-74d5c4355636
Görbitz, Carl Henrik
bd88808d-a53f-40d1-ba40-43f11edc412f
Dalhus, Bjørn
8d312725-603a-44cf-95dc-b85963bff2fc
Day, Graeme M.
e3be79ba-ad12-4461-b735-74d5c4355636

Görbitz, Carl Henrik, Dalhus, Bjørn and Day, Graeme M. (2010) Pseudoracemic amino acid complexes: blind predictions for flexible two-component crystals. Physical Chemistry Chemical Physics, 12 (30), 8466-8477. (doi:10.1039/C004055J).

Record type: Article

Abstract

Ab initio prediction of the crystal packing in complexes between two flexible molecules is a particularly challenging computational chemistry problem. In this work we present results of single crystal structure determinations as well as theoretical predictions for three 1 ? 1 complexes between hydrophobic L- and D-amino acids (pseudoracemates), known from previous crystallographic work to form structures with one of two alternative hydrogen bonding arrangements. These are accurately reproduced in the theoretical predictions together with a series of patterns that have never been observed experimentally. In this bewildering forest of potential polymorphs, hydrogen bonding arrangements and molecular conformations, the theoretical predictions succeeded, for all three complexes, in finding the correct hydrogen bonding pattern. For two of the complexes, the calculations also reproduce the exact space group and side chain orientations in the best ranked predicted structure. This includes one complex for which the observed crystal packing clearly contradicted previous experience based on experimental data for a substantial number of related amino acid complexes. The results highlight the significant recent advances that have been made in computational methods for crystal structure prediction.



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More information

Published date: 11 May 2010
Additional Information: This article is part of the collection: Solid State Structure Prediction
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Computational Systems Chemistry

Identifiers

Local EPrints ID: 343429
URI: http://eprints.soton.ac.uk/id/eprint/343429
ISSN: 1463-9076
PURE UUID: 18544eef-0f48-4882-8450-7d85d43abd92
ORCID for Graeme M. Day: ORCID iD orcid.org/0000-0001-8396-2771

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Date deposited: 08 Oct 2012 10:33
Last modified: 15 Mar 2024 03:44

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Contributors

Author: Carl Henrik Görbitz
Author: Bjørn Dalhus
Author: Graeme M. Day ORCID iD

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