title: Incrementally increasing the length of a peptide backbone: effect on macrocyclisation efficiency.
abstract: Three novel analogues of the cyclic pentapeptide sansalvamide A have been synthesised in high yield. A leucine residue in the lead compound is replaced with either a glycine, β-alanine or GABA residue, and the corresponding linear precursor peptides are found to cyclise with dramatically improved efficiency. This correlates with an increase in the effective molarity (EM) of the cyclisation reactions.
authors.affiliation: School of Chemistry, UNSW Australia, Sydney, NSW 2052, Australia. l.hunter@unsw.edu.au.
authors.forename: Md Iqbal
authors.initials: MI
authors.lastname: Ahmed
authors.forename: Jason B
authors.initials: JB
authors.lastname: Harper
authors.forename: Luke
authors.initials: L
authors.lastname: Hunter
mesh_terms: D016227:Benzoquinones / Q000494:pharmacology; D045744:Cell Line, Tumor; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D047630:Depsipeptides / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D047029:Lactams, Macrocyclic / Q000494:pharmacology; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D016227:Benzoquinones; D047630:Depsipeptides; D047029:Lactams, Macrocyclic; D010456:Peptides, Cyclic; C119376:sansalvamide A; C561693:unguisin A; C112765:tanespimycin