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• W4250227007 abstract "Abstract Oxyvinylglycines are a family of nonproteinogenic amino acids featuring an essential vinyl ether conferring mechanism‐based inhibition of pyridoxal phosphate enzymes. The gene clusters for a few oxyvinylglycines are known, yet the biosynthetic origin of the vinyl ether is elusive. The in vitro biosynthesis of methoxyvinylglycine or l ‐2‐amino‐4‐methoxy‐ trans ‐3‐butenoic acid (AMB) is reported. It is shown that AMB is made from glutamate as an alanyl‐AMB dipeptide and the rationale is provided for the N‐term Ala. Using a chemical capture method, the order and timing of the modifications on non‐ribosomal peptide synthetase (NRPS)‐bound substrates was determined, including a cryptic hydroxylation of the Glu β‐carbon. Eliminating this hydroxy group likely generates a key α,β‐dehydroamino acid intermediate that facilitates decarboxylation. This work sheds light on vinyl ether biosynthesis and uncovers new NRPS chemistry." @default.
• W4250227007 created "2022-05-12" @default.
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• W4250227007 date "2018-05-08" @default.
• W4250227007 modified "2023-09-26" @default.
• W4250227007 title "In Vitro Biosynthesis of the Nonproteinogenic Amino Acid Methoxyvinylglycine" @default.
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• W4250227007 doi "https://doi.org/10.1002/ange.201713419" @default.
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