title: Conformational analysis of peptides and glycopeptides derived from the consensus sequence for β-O-glucosylation.
abstract: Cys-Xxx-Ser-Xxx-Pro-Cys (Xxx= any amino acid but Pro) is the most common sequence present in naturally occurring peptides and proteins glycosylated with β-O-glucose (β-O-Glc). Taking into account the lack of studies concerning the spatial disposition of this sequence, we have synthesized and analyzed, in aqueous solution, the conformational behavior of peptides and a glycopeptide derived from the particular fragment Cys-Ala-Ser-Ser-Pro-Cys. This sequence is found in the crystal structure of the complex of blood coagulation factor VIIa with soluble tissue factor. Our studies, based on the use of NOESY experiments in combination with molecular dynamics (MD) simulations, indicate that for this particular fragment, initially characterized by a type I β-turn motif, the glycosylation with β-O-Glc forces the peptide backbone into an extended conformation. This conformation is stabilized by the presence of both hydrogen bonds and water pockets between the peptide and the sugar moieties.
authors.forename: Victor J
authors.initials: VJ
authors.lastname: Somovilla
authors.forename: Nuria
authors.initials: N
authors.lastname: Martinez-Sáez
authors.forename: Alberto
authors.initials: A
authors.lastname: Fernández-Tejada
authors.forename: Beatríz G
authors.initials: BG
authors.lastname: de la Torre
authors.forename: David
authors.initials: D
authors.lastname: Andreu
authors.forename: Jesús
authors.initials: J
authors.lastname: Jimenez-Barbero
authors.forename: Juan
authors.initials: J
authors.lastname: L Asensio
authors.forename: Alberto
authors.initials: A
authors.lastname: Avenoza
authors.forename: Jesus H
authors.initials: JH
authors.lastname: Busto
authors.forename: Francisco
authors.initials: F
authors.lastname: Corzana
authors.affiliation: Departamento de Quimica, Universidad de La Rioja, Centro de Investigación en Síntesis Quimica, C/ Madre de Dios, 51. 26006 Logrono (La Rioja), Spain. francisco.corzana@unirioja.es.
authors.forename: Jesus M
authors.initials: JM
authors.lastname: Peregrina
mesh_terms: D020816:Amino Acid Motifs; D016384:Consensus Sequence; D015942:Factor VIIa / Q000737:chemistry; D005947:Glucose / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D011485:Protein Binding; D017433:Protein Structure, Secondary; D013925:Thromboplastin / Q000737:chemistry; D014867:Water / Q000737:chemistry
chemical_list: D006020:Glycopeptides; D010455:Peptides; D014867:Water; D013925:Thromboplastin; D015942:Factor VIIa; D005947:Glucose