The aqueous and crystalline forms of L-alanine zwitterion
The structural properties of L-alanine amino acid in aqueous solution and in crystalline phase have been studied by means of density-functional electronic-structure and molecular dynamics simulations. The solvated zwitterionic structure of L-alanine (+NH3-C2H4-COO-) was systematically compared to th...
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| Format: | Journal Article |
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American Scientific Publishers
2008
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| Online Access: | http://www.ingentaconnect.com/content/asp/jctn/2008/00000005/00000003/art00003 http://hdl.handle.net/20.500.11937/42699 |
| _version_ | 1848756492366249984 |
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| author | Degtyarenko, I. Jalkanen, Karl Gurtovenko, A. Nieminen, R. |
| author_facet | Degtyarenko, I. Jalkanen, Karl Gurtovenko, A. Nieminen, R. |
| author_sort | Degtyarenko, I. |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | The structural properties of L-alanine amino acid in aqueous solution and in crystalline phase have been studied by means of density-functional electronic-structure and molecular dynamics simulations. The solvated zwitterionic structure of L-alanine (+NH3-C2H4-COO-) was systematically compared to the structure of its zwitterionic crystalline analogue acquired from both computer simulations and experiments. It turns out that the structural properties of an alanine molecule in aqueous solution can differ significantly from those in crystalline phase, these differences being mainly attributed to hydrogen bonding interactions. In particular, we found that the largest difference between the two alanine forms can be seen for the orientation and bond lengths of the carboxylate (COO-) group: in aqueous solutionthe C-O bond lengths appear to strongly correlate with the number of water molecules which form hydrogen bonds with the COO- group. Furthermore, the hydrogen bond lengths are shorter and the hydrogen bond angles are larger for L-alanine in water as compared to crystal. Overall, our findings strongly suggest that the generally accepted approach of extending the structural information acquired from crystallographic data to a L-alanine molecule in aqueous solution should be used with caution. |
| first_indexed | 2025-11-14T09:13:04Z |
| format | Journal Article |
| id | curtin-20.500.11937-42699 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T09:13:04Z |
| publishDate | 2008 |
| publisher | American Scientific Publishers |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-426992017-01-30T15:01:31Z The aqueous and crystalline forms of L-alanine zwitterion Degtyarenko, I. Jalkanen, Karl Gurtovenko, A. Nieminen, R. crystal structure alanine zwitterion aqueous solution The structural properties of L-alanine amino acid in aqueous solution and in crystalline phase have been studied by means of density-functional electronic-structure and molecular dynamics simulations. The solvated zwitterionic structure of L-alanine (+NH3-C2H4-COO-) was systematically compared to the structure of its zwitterionic crystalline analogue acquired from both computer simulations and experiments. It turns out that the structural properties of an alanine molecule in aqueous solution can differ significantly from those in crystalline phase, these differences being mainly attributed to hydrogen bonding interactions. In particular, we found that the largest difference between the two alanine forms can be seen for the orientation and bond lengths of the carboxylate (COO-) group: in aqueous solutionthe C-O bond lengths appear to strongly correlate with the number of water molecules which form hydrogen bonds with the COO- group. Furthermore, the hydrogen bond lengths are shorter and the hydrogen bond angles are larger for L-alanine in water as compared to crystal. Overall, our findings strongly suggest that the generally accepted approach of extending the structural information acquired from crystallographic data to a L-alanine molecule in aqueous solution should be used with caution. 2008 Journal Article http://hdl.handle.net/20.500.11937/42699 http://www.ingentaconnect.com/content/asp/jctn/2008/00000005/00000003/art00003 American Scientific Publishers restricted |
| spellingShingle | crystal structure alanine zwitterion aqueous solution Degtyarenko, I. Jalkanen, Karl Gurtovenko, A. Nieminen, R. The aqueous and crystalline forms of L-alanine zwitterion |
| title | The aqueous and crystalline forms of L-alanine zwitterion |
| title_full | The aqueous and crystalline forms of L-alanine zwitterion |
| title_fullStr | The aqueous and crystalline forms of L-alanine zwitterion |
| title_full_unstemmed | The aqueous and crystalline forms of L-alanine zwitterion |
| title_short | The aqueous and crystalline forms of L-alanine zwitterion |
| title_sort | aqueous and crystalline forms of l-alanine zwitterion |
| topic | crystal structure alanine zwitterion aqueous solution |
| url | http://www.ingentaconnect.com/content/asp/jctn/2008/00000005/00000003/art00003 http://hdl.handle.net/20.500.11937/42699 |