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Conformational behavior of phenylglycines and hydroxyphenylglycines and non-planarity of phenyl rings

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Title Conformational behavior of phenylglycines and hydroxyphenylglycines and non-planarity of phenyl rings
 
Creator Nandel, Fateh S
Shafique, Mohd
 
Subject Conformation
Aromatic ring
Planarity
Lone pair∙∙π interactions
Molecular dynamics simulations
Phenylglycines
Hydroxyphenylglycines
 
Description 350-357
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.
 
Date 2014-11-12T11:07:29Z
2014-11-12T11:07:29Z
2014-10
 
Type Article
 
Identifier 0975-0959 (Online); 0301-1208 (Print)
http://hdl.handle.net/123456789/29892
 
Language en_US
 
Rights CC Attribution-Noncommercial-No Derivative Works 2.5 India
 
Publisher NISCAIR-CSIR, India
 
Source IJBB Vol.51(5) [October 2014]