Synthesis and conformational studies of novel cyclic peptides constrained into a 3 10 helical structure by a heterochiral D-pro-L-pro dipeptide template.
An acyclic tripeptide based on a heterochiral D-pro-L-pro template shows a propensity to exist as a 3(10) helical conformation and can be cyclized, via ring-closing metathesis, to the corresponding cyclic tetrapeptides without disrupting the helical conformations in CDCl(3) as well as in DMSO-d(6) solutions. The detailed conformational studies were carried out by using NMR spectroscopy, X-ray crystallography, molecular dynamic simulations, and circular dichroism spectroscopy.
Rao
I Nageshwara
IN
Dr. Reddy's Laboratories, Discovery Research, Bollaram Road, Miyapur, Hyderabad 500 050, India.
Boruah
Anima
A
Kumar
S Kiran
SK
Kunwar
A C
AC
Devi
A Sivalakshmi
AS
Vyas
K
K
Ravikumar
Krishnan
K
Iqbal
Javed
J
D000577:Amides / Q000737:chemistry; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D003500:Cyclization; D004151:Dipeptides / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D019906:Nuclear Magnetic Resonance, Biomolecular; D009842:Oligopeptides / Q000138:chemical synthesis*; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000577:Amides; D004151:Dipeptides; D009842:Oligopeptides; D010456:Peptides, Cyclic; C448039:prolyl-proline