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.
UMR 176 CNRS, Laboratoire de Pharmacochimie, Institut Curie Section de Recherche, Batiment 110, Centre Universitaire, 91405 Orsay, France.
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Motorina
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Huel
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Quiniou
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Grierson
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