Phenylisoserine: a versatile amino acid for the construction of novel beta-peptide structures.
The N-Boc O-tert-butyldimethysilyl-substituted hexa-beta-peptide methyl ester 18 was constructed from the O-TBS ether of (-)-(2R, 3S)-phenylisoserine. By NMR, it was determined that this homo beta-peptide adopts a highly stable beta-strand-type secondary structure in chloroform solution, which is stabilized by both hydrophobic interactions involving the OTBS methyl groups of residues i and i + 2, and inter-(five-membered)/intra (six-membered)-residue H-bonding interactions. These interactions are systematically repeated along the peptide chain and, thereby, operate in concert to stabilize the observed conformation of 18.
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UMR 176 CNRS, Laboratoire de Pharmacochimie, Institut Curie Section de Recherche, Batiment 110, Centre Universitaire, 91405 Orsay, France.
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Quiniou
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D002942:Circular Dichroism; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011487:Protein Conformation; D017433:Protein Structure, Secondary; D012694:Serine / Q000031:analogs & derivatives / Q000737:chemistry*; D013499:Surface Properties
D010455:Peptides; D012694:Serine; C010286:beta-phenylisoserine