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Synthesis of endolides A and B: naturally occurring N-methylated cyclic tetrapeptides.

ABSTRACT: Endolides A and B are naturally occurring, N-methylated, cyclic tetrapeptides possessing an unusual 3-(3-furyl)alanine amino acid and outstanding biological profiles. 1-Propanephosphonic anhydride (T3P) was used to mediate a solution-phase cyclisation reaction of the linear tetrapeptides, thus achieving the first syntheses of both endolides A and B. The stereoselectivity of the tetrapeptide cyclisation reactions was found to be reagent-controlled, and was independent of the C-terminal configuration of the linear peptide starting materials.

SUBMITTER: Davison EK

PROVIDER: S-EPMC6533800 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Synthesis of endolides A and B: naturally occurring <i>N</i>-methylated cyclic tetrapeptides.

Davison Emma K EK Cameron Alan J AJ Harris Paul W R PWR Brimble Margaret A MA

MedChemComm 20190305 5

Endolides A and B are naturally occurring, <i>N</i>-methylated, cyclic tetrapeptides possessing an unusual 3-(3-furyl)alanine amino acid and outstanding biological profiles. 1-Propanephosphonic anhydride (T3P) was used to mediate a solution-phase cyclisation reaction of the linear tetrapeptides, thus achieving the first syntheses of both endolides A and B. The stereoselectivity of the tetrapeptide cyclisation reactions was found to be reagent-controlled, and was independent of the C-terminal con ...[more]

PMID: 31191859

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