title: Efficient macrocyclization of U-turn preorganized peptidomimetics: the role of intramolecular H-bond and solvophobic effects.
abstract: Simple peptidomimetic molecules derived from amino acids were reacted with meta- and para-bis(bromomethyl)benzene in acetonitrile to very efficiently yield macrocyclic structures. The cyclization reaction does not require high dilution techniques and seems to be insensitive to the size of the formed macrocycle. The analysis of data obtained by (1)H NMR, single-crystal X-ray diffraction, fluorescence measurements, and molecular mechanics indicate that folded conformations can preorganize the system for an efficient cyclization. The role played by intramolecular hydrogen-bonding and solvophobic effects in the presence of folded conformations is analyzed.
authors.affiliation: Department of Inorganic and Organic Chemistry, University Jaume, I. E-12080 Castellón, Spain.
authors.forename: Jorge
authors.initials: J
authors.lastname: Becerril
authors.forename: Michael
authors.initials: M
authors.lastname: Bolte
authors.forename: M Isabel
authors.initials: MI
authors.lastname: Burguete
authors.forename: Francisco
authors.initials: F
authors.lastname: Galindo
authors.forename: Enrique
authors.initials: E
authors.lastname: García-España
authors.forename: Santiago V
authors.initials: SV
authors.lastname: Luis
authors.forename: Juan F
authors.initials: JF
authors.lastname: Miravet
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D040761:Biomimetic Materials / Q000737:chemistry*; D003198:Computer Simulation; D003500:Cyclization; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010455:Peptides / Q000737:chemistry*; D017510:Protein Folding; D012997:Solvents; D013050:Spectrometry, Fluorescence; D014050:Toluene / Q000031:analogs & derivatives; D014961:X-Ray Diffraction
chemical_list: D000577:Amides; D000596:Amino Acids; D010455:Peptides; D012997:Solvents; D014050:Toluene