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| DC Field | Value | Language |
|---|---|---|
| dc.contributor.author | Nandel, Fateh S | - |
| dc.contributor.author | Shafique, Mohd | - |
| dc.date.accessioned | 2014-11-12T11:07:29Z | - |
| dc.date.available | 2014-11-12T11:07:29Z | - |
| dc.date.issued | 2014-10 | - |
| dc.identifier.issn | 0975-0959 (Online); 0301-1208 (Print) | - |
| dc.identifier.uri | http://hdl.handle.net/123456789/29892 | - |
| dc.description | 350-357 | en_US |
| dc.description.abstract | The non-proteinogenic
amino acids — phenylglycine (PG) and hydroxyphenylglycine (HPG) are crucial
components of certain peptidic natural products and are important for the
preparation of various medicines. In this, study, the conformation of model
dipeptides Ac-X-NHMe of PG, p-HPG and
3, 5-di-hydroxyphenylglycine (3, 5-DHPG) was studied both in R and S form by quantum
mechanical (QM) and molecular dynamics approaches. On the energy scale, the
conformational states of these molecules in both the R and S were found to be degenerate by QM studies, stabilized by
non-covalent interactions like carbonyl--carbonyl interactions, carbonyl-lp··π
(aromatic ring) interactions etc. These interactions disappeared/weakened due
to interaction of water molecules with carbonyl groups of backbone in
simulation and water was found to interact with the aromatic ring through Ow-H··π
or Owlp··π interactions. The degeneracy of conformational states was
lifted in favor of R-form of PG and DHPG and water molecules
interactions with aromatic ring led to non-planarity of the aromatic ring. In
simulation studies, irrespective of the starting geometry, the  ,  values for the R form correspond to inverse b/inverse collagen region and for the S-form, the , values correspond to b/collagen region i.e., adopt single
conformation. The obtained results were in conformity with the CD spectroscopic
data on D-PG and
D-p-HPG.
The conformational behavior of the unusual amino acids might be of great help
in designing of bioactive peptides/peptide based drugs to be realized in single
conformation – an essential requirement.
| en_US |
| dc.language.iso | en_US | en_US |
| dc.publisher | NISCAIR-CSIR, India | en_US |
| dc.rights |  CC Attribution-Noncommercial-No Derivative Works 2.5 India | en_US |
| dc.source | IJBB Vol.51(5) [October 2014] | en_US |
| dc.subject | Conformation | en_US |
| dc.subject | Aromatic ring | en_US |
| dc.subject | Planarity | en_US |
| dc.subject | Lone pair∙∙π interactions | en_US |
| dc.subject | Molecular dynamics simulations | en_US |
| dc.subject | Phenylglycines | en_US |
| dc.subject | Hydroxyphenylglycines | en_US |
| dc.title | Conformational behavior of phenylglycines and hydroxyphenylglycines and non-planarity of phenyl rings | en_US |
| dc.type | Article | en_US |
| Appears in Collections: | IJBB Vol.51(5) [October 2014] | |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| IJBB 51(5) 350-357.pdf | 258.46 kB | Adobe PDF | View/Open |
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