Journal
CHEMICAL COMMUNICATIONS
Volume 59, Issue 9, Pages 1165-1168Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc06345j
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This report demonstrates that the biosynthesis of lanthipeptides containing the d-allo-l-MeLan macrocycle proceeds through (E)-Dhb intermediates formed by net syn-elimination of l-Thr.
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.
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