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Solid-Phase Synthesis of Biaryl Cyclic Lipopeptides Derived from Arylomycins.

ABSTRACT: An efficient approach for the solid-phase synthesis of N-methylated tailed biaryl cyclic lipopeptides based on the structure of arylomycins was established. Each of these analogues incorporates an N-terminal linear lipopeptide attached to a biaryl cyclic tripeptide containing a Phe-Tyr, a Tyr-Tyr, or a His-Tyr linkage. This methodology first involved an intramolecular Suzuki-Miyaura arylation of a linear peptidyl resin incorporating the corresponding halogenated amino acid at the N-terminus and a boronotyrosine at the C-terminus. After N-methylation of the resulting biaryl cyclic peptidyl resin, the N-methylated lipopeptidyl tail was then assembled. The biaryl cyclic lipopeptides were purified and characterized.

SUBMITTER: Ng-Choi I

PROVIDER: S-EPMC7496001 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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Solid-Phase Synthesis of Biaryl Cyclic Lipopeptides Derived from Arylomycins.

Ng-Choi Iteng I Figueras Eduard E Oliveras Àngel À Feliu Lidia L Planas Marta M

ACS omega 20200904 36

An efficient approach for the solid-phase synthesis of N-methylated tailed biaryl cyclic lipopeptides based on the structure of arylomycins was established. Each of these analogues incorporates an N-terminal linear lipopeptide attached to a biaryl cyclic tripeptide containing a Phe-Tyr, a Tyr-Tyr, or a His-Tyr linkage. This methodology first involved an intramolecular Suzuki-Miyaura arylation of a linear peptidyl resin incorporating the corresponding halogenated amino acid at the N-terminus and ...[more]

PMID: 32954193

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