title: Pseudo-prolines (psi Pro) for accessing "inaccessible" peptides.
abstract: Pseudo-prolines (psi Pro) are introduced as a temporary protection technique for serine, threonine and cysteine side chains in standard Fmoc/tBu solid-phase peptide synthesis (SPPS). The incorporation of these novel building blocks into a growing peptide chain proceeds by means of the coupling of preformed, suitably protected psi Pro dipeptides. For the example of representative model peptides used in protein de novo design, the potential of psi Pro to solubilize otherwise sparingly or completely insoluble peptides is demonstrated. Because of their intrinsic propensity for preventing peptide aggregation and beta-sheet formation, pseudo-prolines offer new possibilities for accessing large peptides by convergent strategies and chemoselective ligation techniques.
authors.affiliation: Institute of Organic Chemistry, University of Lausanne, Switzerland.
authors.forename: M
authors.initials: M
authors.lastname: Mutter
authors.forename: A
authors.initials: A
authors.lastname: Nefzi
authors.forename: T
authors.initials: T
authors.lastname: Sato
authors.forename: X
authors.initials: X
authors.lastname: Sun
authors.forename: F
authors.initials: F
authors.lastname: Wahl
authors.forename: T
authors.initials: T
authors.lastname: Wöhr
mesh_terms: D000595:Amino Acid Sequence; D001559:Benzhydryl Compounds; D002625:Chemistry, Organic / Q000295:instrumentation; D002851:Chromatography, High Pressure Liquid; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D017433:Protein Structure, Secondary; D012117:Resins, Synthetic; D013329:Structure-Activity Relationship; D013698:Templates, Genetic; D013844:Thiazoles / Q000737:chemistry*
chemical_list: C030545:4-methylbenzhydrylamine resin; D001559:Benzhydryl Compounds; D010080:Oxazoles; D010455:Peptides; D012117:Resins, Synthetic; D013844:Thiazoles