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- Title
The Ant-Pro Reverse-Turn Motif. Structural Features and Conformational Characteristics.
- Authors
Thorat, Vijaykumar H.; Ingole, Tukaram S.; Vijayadas, Kuruppanthara N.; Nair, Roshna V.; Kale, Sangram S.; Ramesh, Veera V. E.; Davis, Hilda C.; Prabhakaran, Panchami; Gonnade, Rajesh G.; Gawade, Rupesh L.; Puranik, Vedavati G.; Rajamohanan, Pattuparambil R.; Sanjayan, Gangadhar J.
- Abstract
This article details the characteristic conformational features of the Ant-Pro reverse turn - a folded pseudo β-turn motif that displays a closed nine-membered-ring hydrogen-bonded network involving just two amino acid residues, namely anthranilic acid (Ant; a constrained β-amino acid), and proline (Pro; a constrained α-amino acid). The results from the extensive investigation of ten crystal structures and their NMR conformations in the solution state provide a clear idea about the conformational characteristics of the Ant-Pro reverse turn. The Ant and Pro residues, which form the turn segment, maintain a perfect antiperiplanar orientation throughout, leaving little possibility for the formation of the otherwise possible six-membered hydrogen-bonding that requires a coplanar disposition of the two amino acid residues, as clearly evident from investigation of several crystal structures. The closed hydrogen-bonded network observed in the Ant-Pro reverse turn motif, formed in the forward direction of the sequence (1→2 amino acid interactions) involving only two amino acid residues, is in stark contrast to the native β-turns that involve four residues to form hydrogen-bonded network featuring backward 1←4 amino acid interactions. The readily available two-residue Ant-Pro motif raises the possibility of a practical utility, particularly in the application of rigidifying flexible peptide backbones by inserting the robust Ant-Pro reverse turn motifs into their backbone.
- Subjects
HYDROGEN bonding; AMINO acids; CRYSTAL structure; AMINOBENZOIC acids; ORGANIC acids
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 17, p3529
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201201739