title: Synthesis of Psychrophilin E.
abstract: The first total synthesis of psychrophilin E, a potent antiproliferative cyclic tripeptide isolated from Aspergillus versicolor ZLN-60, is reported herein. Key features of the synthesis include the installation of an amide bond between the indole-nitrogen of tryptophan and an anthranilic acid residue, and a high yielding macrolactamization of the linear tripeptide to the desired macrocycle.
authors.affiliation: School of Chemical Sciences, The University of Auckland , 23 Symonds Street, Auckland, New Zealand.|Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland , 3 Symonds Street, Auckland, New Zealand.
authors.forename: Sarah T Y
authors.initials: ST
authors.lastname: Ngen
authors.affiliation: School of Chemical Sciences, The University of Auckland , 23 Symonds Street, Auckland, New Zealand.|Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland , 3 Symonds Street, Auckland, New Zealand.
authors.forename: Harveen
authors.initials: H
authors.lastname: Kaur
authors.affiliation: School of Chemical Sciences, The University of Auckland , 23 Symonds Street, Auckland, New Zealand.|Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland , 3 Symonds Street, Auckland, New Zealand.
authors.forename: Paul A
authors.initials: PA
authors.lastname: Hume
authors.affiliation: School of Chemical Sciences, The University of Auckland , 23 Symonds Street, Auckland, New Zealand.|Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland , 3 Symonds Street, Auckland, New Zealand.
authors.forename: Daniel P
authors.initials: DP
authors.lastname: Furkert
authors.affiliation: School of Chemical Sciences, The University of Auckland , 23 Symonds Street, Auckland, New Zealand.|Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland , 3 Symonds Street, Auckland, New Zealand.
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble
mesh_terms: D001230:Aspergillus / Q000737:chemistry; D007211:Indoles / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D021241:Spectrometry, Mass, Electrospray Ionization; D014364:Tryptophan / Q000737:chemistry; D062367:ortho-Aminobenzoates / Q000737:chemistry
chemical_list: D007211:Indoles; D010456:Peptides, Cyclic; D062367:ortho-Aminobenzoates; C000592196:psychrophilin E; C031385:anthranilic acid; D014364:Tryptophan; D009584:Nitrogen