title: Introducing an Asp-Pro linker in the synthesis of random one-bead-one-compound hexapeptide libraries compatible with ESI-MS analysis.
abstract: A random hexapeptide library (one-bead-one-compound), containing sixteen amino acids (16(6) different sequences) was synthesized on a Tentagel resin previously modified with a dipeptide linker (Asp-Pro). This peptide bond is highly susceptible to cleavage under mild acidic conditions in a salt-free solution prepared with H(2)(16)O/H(2)(18)O (60/40% v/v). In the hydrolysis, hexapeptides are released with an additional Asp residue partially labeled with (18)O at the C-terminus. These conditions are fully compatible with ESI-MS analysis and facilitate sequencing by MS, as N- and C-terminal ions can be easily differentiated in MS/MS spectra. The peptides were sequenced manually and also with de novo sequencing programs, and identifying them in a database containing all possible heptapeptide sequences or in a filtered database. The proposed strategy is also compatible with stepwise Edman degradation using either intact beads or the released free peptides.
authors.affiliation: Department of Chemical Synthesis, Division of Physical-Chemistry, Center for Genetic Engineering and Biotechnology, Havana, Cuba.
authors.forename: Yordanka
authors.initials: Y
authors.lastname: Masforrol
authors.forename: Jeovanis
authors.initials: J
authors.lastname: Gil
authors.forename: Luis Javier
authors.initials: LJ
authors.lastname: González
authors.forename: Yasset
authors.initials: Y
authors.lastname: Pérez-Riverol
authors.forename: Jorge
authors.initials: J
authors.lastname: Fernández-de-Cossío
authors.forename: Aniel
authors.initials: A
authors.lastname: Sánchez
authors.forename: Lázaro Hiram
authors.initials: LH
authors.lastname: Betancourt
authors.forename: Hilda Elisa
authors.initials: HE
authors.lastname: Garay
authors.forename: Ania
authors.initials: A
authors.lastname: Cabrales
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
authors.forename: Hongqian
authors.initials: H
authors.lastname: Yang
authors.forename: Roman A
authors.initials: RA
authors.lastname: Zubarev
authors.forename: Vladimir
authors.initials: V
authors.lastname: Besada
authors.forename: Osvaldo Reyes
authors.initials: OR
authors.lastname: Acosta
mesh_terms: D000595:Amino Acid Sequence; D020650:Combinatorial Chemistry Techniques; D004151:Dipeptides / Q000737:chemistry*; D008969:Molecular Sequence Data; D019151:Peptide Library; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D004151:Dipeptides; D019151:Peptide Library; C070752:aspartyl-proline