title: Site-selective modification of peptides: From "customizable units" to novel α-aryl and α-alkyl glycine derivatives, and components of branched peptides.
abstract: The creation of peptide libraries by site-selective modification of a few peptide substrates would increase the efficiency of discovery processes, but still is a real synthetic challenge. The site-selective modification of small peptides at serine or threonine residues, by using a short scission-addition procedure, allows the preparation of peptides with unnatural α-aryl glycines. In a similar way, the scission of hydroxyproline residues is the key step in the production of optically pure α-alkyl glycines which are precursors or components of branched peptides. With these versatile processes, a single peptide can be transformed into a variety of peptide derivatives. The process takes place under mild conditions, and good global yields are obtained. © 2015 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 104: 650-662, 2015.
authors: Instituto de Productos Naturales y Agrobiología CSIC, Avda. Astrofísico Fco. Sánchez 3, 38206 La Laguna, Tenerife, Spain.
authors: Iván
authors: I
authors: Romero-Estudillo
authors: Instituto de Productos Naturales y Agrobiología CSIC, Avda. Astrofísico Fco. Sánchez 3, 38206 La Laguna, Tenerife, Spain.
authors: Carlos
authors: C
authors: Saavedra
authors: Instituto de Productos Naturales y Agrobiología CSIC, Avda. Astrofísico Fco. Sánchez 3, 38206 La Laguna, Tenerife, Spain.
authors: Alicia
authors: A
authors: Boto
authors: Instituto de Investigaciones Químicas CSIC-USE, Avda. Américo Vespucio 49, Isla de la Cartuja,, 41092, Sevilla, Spain.
authors: Eleuterio
authors: E
authors: Álvarez
mesh_terms: D005998:Glycine / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D012694:Serine / Q000737:chemistry; D054852:Small Molecule Libraries / Q000138:chemical synthesis / Q000737:chemistry; D013379:Substrate Specificity; D013912:Threonine / Q000737:chemistry
chemical_list: D010455:Peptides; D054852:Small Molecule Libraries; D013912:Threonine; D012694:Serine; D005998:Glycine
keywords: amino acids; organic synthesis; peptides; sequential processes; site-selective modification