title: An evaluation of peptide-bond isosteres.
abstract: Peptide-bond isosteres can enable a deep interrogation of the structure and function of a peptide or protein by amplifying or attenuating particular chemical properties. In this Minireview, the electronic, structural, and conformational attributes of four such isosteres-thioamides, esters, alkenes, and fluoroalkenes-are examined in detail. In particular, the ability of these isosteres to partake in noncovalent interactions is compared with that of the peptide bond. The consequential perturbations provide a useful tool for chemical biologists to reveal new structure-function relationships, and to endow peptides and proteins with desirable attributes.
authors.affiliation: Graduate Program in Biophysics, University of Wisconsin-Madison, Madison, WI 53706-1534, USA.
authors.forename: Amit
authors.initials: A
authors.lastname: Choudhary
authors.forename: Ronald T
authors.initials: RT
authors.lastname: Raines
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000595:Amino Acid Sequence; D055731:Carbohydrate Biochemistry / Q000379:methods*; D004583:Electrons; D004952:Esters / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry; D006860:Hydrogen Bonding; D007536:Isomerism; D008958:Models, Molecular; D018716:Molecular Mimicry; D010455:Peptides / Q000737:chemistry*; D011487:Protein Conformation; D055672:Static Electricity; D013816:Thermodynamics; D013854:Thioamides / Q000737:chemistry*
chemical_list: D000475:Alkenes; D004952:Esters; D010455:Peptides; D013854:Thioamides; D005459:Fluorides