title: N,O-isopropylidenated threonines as tools for peptide cyclization: application to the synthesis of mahafacyclin B.
abstract: [structure: see text] The influence of a single N,O-isopropylidenated threonine turn-inducer on the cyclization of a linear heptapeptide precursor to mahafacyclin B has been investigated. Incorporation of an N,O-isopropylidenated threonine more than doubles the head-to-tail cyclization yield. The N,O-isopropylidene grouping is then readily disassembled to give the antimalarial cyclic peptide in high yield.
authors.affiliation: School of Chemistry, The University of Sydney, 2006 NSW, Australia.
authors.forename: Nima
authors.initials: N
authors.lastname: Sayyadi
authors.forename: Danielle
authors.initials: D
authors.lastname: Skropeta
authors.forename: Katrina A
authors.initials: KA
authors.lastname: Jolliffe
mesh_terms: D000595:Amino Acid Sequence; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013912:Threonine / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: D010455:Peptides; D010456:Peptides, Cyclic; C512387:mahafacyclin B; D013912:Threonine