Conformationally constrained aliphatic-aromatic amino-acid-conjugated hybrid foldamers with periodic beta-turn motifs.
In this note, we describe the design, synthesis, and structural studies of novel hybrid foldamers derived from Aib-Pro-Adb building blocks that display repeat beta-turn structure motif. The foldamer having a conformationally constrained aliphatic-aromatic amino acid conjugate adopts a well-defined, compact, three-dimensional structure, governed by a combined conformational restriction imposed by the individual amino acids with which it is made of. Conformational investigations by single-crystal X-ray and solution-state NMR studies were undertaken to investigate the conformational preference of these foldamers with a hetero-backbone. Our findings suggest that constrained aliphatic-aromatic amino acid conjugates would offer new avenues for the de novo design of hybrid foldamers with distinctive structural architectures.
Srinivas
Deekonda
D
Division of Organic Synthesis, Center for Materials Characterization, and Central NMR Facility, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411 008, India.
Gonnade
Rajesh
R
Ravindranathan
Sapna
S
Sanjayan
Gangadhar J
GJ
D024322:Amino Acids, Aromatic / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005227:Fatty Acids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D017434:Protein Structure, Tertiary; D017186:Titrimetry
D024322:Amino Acids, Aromatic; D005227:Fatty Acids