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syn-Elimination of glutamylated threonine in lanthipeptide biosynthesis.

ABSTRACT: Methyllanthionine (MeLan) containing macrocycles are key structural features of lanthipeptides. They are formed typically by anti-elimination of L-Thr residues followed by cyclization of L-Cys residues onto the (Z)-dehydrobutyrine (Dhb) intermediates. In this report we demonstrate that the biosynthesis of lanthipeptides containing the D-allo-L-MeLan macrocycle such as the morphogenetic lanthipeptide SapT proceeds through (E)-Dhb intermediates formed by net syn-elimination of L-Thr.

SUBMITTER: Sarksian R

PROVIDER: S-EPMC9890492 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature

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syn-Elimination of glutamylated threonine in lanthipeptide biosynthesis.

Sarksian Raymond R Zhu Lingyang L van der Donk Wilfred A WA

Chemical communications (Cambridge, England) 20230126 9

Methyllanthionine (MeLan) containing macrocycles are key structural features of lanthipeptides. They are formed typically by anti-elimination of L-Thr residues followed by cyclization of L-Cys residues onto the (Z)-dehydrobutyrine (Dhb) intermediates. In this report we demonstrate that the biosynthesis of lanthipeptides containing the D-allo-L-MeLan macrocycle such as the morphogenetic lanthipeptide SapT proceeds through (E)-Dhb intermediates formed by net syn- ...[more]

PMID: 36625436

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