title: Reversal of H-bonding direction by N-sulfonation in a synthetic reverse-turn peptide motif.
abstract: This communication depicts an intriguing example of hydrogen-bonding reversal upon introduction of a sulfonamide linkage at the N-terminus of a synthetic reverse-turn peptide motif. The ready availability of two sulfonyl oxygen atoms, as hydrogen-bonding acceptors, combined with the inherent twisted conformation of sulfonamides are seen to act as switches that engage/disengage the hydrogen-bond at the sticky ends/termini.
authors.affiliation: Division of Organic Chemistry, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411 008, India. gj.sanjayan@ncl.res.in.
authors.forename: Kuruppanthara N
authors.initials: KN
authors.lastname: Vijayadas
authors.forename: Amol S
authors.initials: AS
authors.lastname: Kotmale
authors.forename: Shridhar H
authors.initials: SH
authors.lastname: Thorat
authors.forename: Rajesh G
authors.initials: RG
authors.lastname: Gonnade
authors.forename: Roshna V
authors.initials: RV
authors.lastname: Nair
authors.forename: Pattuparambil R
authors.initials: PR
authors.lastname: Rajamohanan
authors.forename: Gangadhar J
authors.initials: GJ
authors.lastname: Sanjayan
mesh_terms: D020816:Amino Acid Motifs; D018360:Crystallography, X-Ray; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D010455:Peptides / Q000737:chemistry; D011108:Polymers / Q000737:chemistry; D017434:Protein Structure, Tertiary; D013449:Sulfonamides / Q000737:chemistry; D013455:Sulfur / Q000737:chemistry*; D013696:Temperature
chemical_list: D010455:Peptides; D011108:Polymers; D013449:Sulfonamides; D013455:Sulfur; D010100:Oxygen; D004121:Dimethyl Sulfoxide