An ab initio exploratory study on the conformational features of the dipeptide MeCO-Ala-Ala-NH-Me in its four different configurations: determination of the behaviour of d-enantiomer amino acids within a peptide chain
Ab initio conformational studies at the RHF/3-21G level of theory were carried out for the dipeptide MeCO-Ala-Ala-NH-Me in its four different configurations (MeCO- l-Ala- l-Ala-NH-Me, MeCO- d-Ala- d-Ala-NH-Me, MeCO- l-Ala- d-Ala-NH-Me and MeCO- d-Ala- l-Ala-NH-Me). From this method the conformations...
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| Published in: | Journal of molecular structure. Theochem Vol. 666; pp. 291 - 301 |
|---|---|
| Main Authors: | , , , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
Elsevier B.V
29-12-2003
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| Abstract | Ab initio conformational studies at the RHF/3-21G level of theory were carried out for the dipeptide MeCO-Ala-Ala-NH-Me in its four different configurations (MeCO-
l-Ala-
l-Ala-NH-Me, MeCO-
d-Ala-
d-Ala-NH-Me, MeCO-
l-Ala-
d-Ala-NH-Me and MeCO-
d-Ala-
l-Ala-NH-Me). From this method the conformations for these dipeptides were found to be β
lγ
l, β
lγ
d, β
lγ
d and β
lγ
l, respectively. Patterns were investigated on Ramachandran maps to identify annihilated critical points among the four dipeptides to determine whether the
d-enantiomer was in fact the ‘mirror image’ of the
l-enantiomer dipeptide in addition to determining the role of the
d-isomer in the peptide chain. The differences in energies for each conformation were also compared between the dipeptides. |
|---|---|
| AbstractList | Ab initio conformational studies at the RHF/3-21G level of theory were carried out for the dipeptide MeCO-Ala-Ala-NH-Me in its four different configurations (MeCO-
l-Ala-
l-Ala-NH-Me, MeCO-
d-Ala-
d-Ala-NH-Me, MeCO-
l-Ala-
d-Ala-NH-Me and MeCO-
d-Ala-
l-Ala-NH-Me). From this method the conformations for these dipeptides were found to be β
lγ
l, β
lγ
d, β
lγ
d and β
lγ
l, respectively. Patterns were investigated on Ramachandran maps to identify annihilated critical points among the four dipeptides to determine whether the
d-enantiomer was in fact the ‘mirror image’ of the
l-enantiomer dipeptide in addition to determining the role of the
d-isomer in the peptide chain. The differences in energies for each conformation were also compared between the dipeptides. |
| Author | Chass, Gregory A Brijbassi, Sonya U Penke, Botond Csizmadia, Imre G Sahai, Michelle A Setiadi, David H |
| Author_xml | – sequence: 1 givenname: Sonya U surname: Brijbassi fullname: Brijbassi, Sonya U email: s_brijbassi@hotmail.com organization: Global Institute of COmputational Molecular and Materials Science (GIOCOMMS), 1422 Edenrose St., Mississiauga, Ont., Canada L5V 1H3 – sequence: 2 givenname: Michelle A surname: Sahai fullname: Sahai, Michelle A email: msahai@giocomms.org organization: Global Institute of COmputational Molecular and Materials Science (GIOCOMMS), 1422 Edenrose St., Mississiauga, Ont., Canada L5V 1H3 – sequence: 3 givenname: David H surname: Setiadi fullname: Setiadi, David H email: dsetiadi@giocomms.org organization: Global Institute of COmputational Molecular and Materials Science (GIOCOMMS), 1422 Edenrose St., Mississiauga, Ont., Canada L5V 1H3 – sequence: 4 givenname: Gregory A surname: Chass fullname: Chass, Gregory A email: gchass@giocomms.org organization: Global Institute of COmputational Molecular and Materials Science (GIOCOMMS), 1422 Edenrose St., Mississiauga, Ont., Canada L5V 1H3 – sequence: 5 givenname: Botond surname: Penke fullname: Penke, Botond email: pbotond@mdche.szote.u-szeged.hu organization: Department of Medical Chemistry, University of Szeged, H-6720 Szeged, Dóm tér 8, Hungary – sequence: 6 givenname: Imre G surname: Csizmadia fullname: Csizmadia, Imre G email: icsizmad@alchemy.chem.utoronto.ca organization: Global Institute of COmputational Molecular and Materials Science (GIOCOMMS), 1422 Edenrose St., Mississiauga, Ont., Canada L5V 1H3 |
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| CitedBy_id | crossref_primary_10_1016_j_comptc_2011_05_023 crossref_primary_10_1002_jcc_20360 crossref_primary_10_1134_S0006350907020029 crossref_primary_10_1021_acs_jctc_5b00911 crossref_primary_10_1016_j_theochem_2005_02_064 crossref_primary_10_1186_s13065_023_01051_9 crossref_primary_10_1021_ct700082f |
| Cites_doi | 10.1002/qua.947 10.1021/ja00016a049 |
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| Keywords | Dipeptides l-Enantiomer Ab initio Protein folding Ramachandran maps d-Enantiomer |
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| References | Daniel, Errington (BIB2) 2003; 6 M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, Ö. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, P. Salvador, J.J. Dannenberg, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M. W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98, Revision A.9, Gaussian, Inc., Pittsburgh PA, 2001. M.A. Sahai, S. Lovas, G.A. Chass, B. Penke, I.G. Csizmadia, J. Mol. Struct. (THEOCHEM), in this issue. Perczel, Angyan, Kajtar, Viviani, Rivail, Marcoccia, Csizmadia (BIB5) 1991; 113 Chass, Sahai, Law, Lovas, Farkes, Perczel, Rivail, Csizmadia (BIB3) 2002; 90 Perczel (10.1016/j.theochem.2003.08.034_BIB5) 1991; 113 10.1016/j.theochem.2003.08.034_BIB4 Daniel (10.1016/j.theochem.2003.08.034_BIB2) 2003; 6 Chass (10.1016/j.theochem.2003.08.034_BIB3) 2002; 90 10.1016/j.theochem.2003.08.034_BIB1 |
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| Title | An ab initio exploratory study on the conformational features of the dipeptide MeCO-Ala-Ala-NH-Me in its four different configurations: determination of the behaviour of d-enantiomer amino acids within a peptide chain |
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