Orthanilic acid-promoted reverse turn formation in peptides.

Sangram S Kale, Gowri Priya, Amol S Kotmale, Rupesh L Gawade, Vedavati G Puranik, P R Rajamohanan, Gangadhar J Sanjayan

Index: Chem. Commun. (Camb.) 49(22) , 2222-4, (2013)

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Abstract

Orthanilic acid (2-aminobenzenesulfonic acid, (S)Ant), an aromatic β-amino acid, has been shown to be highly useful in inducing a folded conformation in peptides. When incorporated into peptide sequences (Xaa-(S)Ant-Yaa), this rigid aromatic β-amino acid strongly imparts a reverse-turn conformation to the peptide backbone, featuring robust 11-membered-ring hydrogen-bonding.