N,O-isopropylidenated threonines as tools for peptide cyclization: application to the synthesis of mahafacyclin B.
[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.
Sayyadi
Nima
N
School of Chemistry, The University of Sydney, 2006 NSW, Australia.
Skropeta
Danielle
D
Jolliffe
Katrina A
KA
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*
D010455:Peptides; D010456:Peptides, Cyclic; C512387:mahafacyclin B; D013912:Threonine