ArticleBiosynthesis of the Unique Amino Acid Side Chain of Butirosin (cas 12772-35-9): Possible Protective-Group Chemistry in an Acyl Carrier Protein-Mediated Pathway

Add time:08/30/2019    Source:sciencedirect.com

SummaryButirosins A and B are naturally occurring aminoglycoside antibiotics that have a (2S)-4-amino-2-hydroxybutyrate (AHBA) side chain. Semisynthetic addition of AHBA to clinically valuable aminoglycoside antibiotics has been shown both to improve their pharmacological properties and to prevent their deactivation by a number of aminoglycoside-modifying enzymes involved in bacterial resistance. We report here that the biosynthesis of AHBA from L-glutamate, encoded within a previously identified butirosin biosynthetic gene cluster, proceeds via intermediates tethered to a specific acyl carrier protein (ACP). Five components of the pathway have been purified and characterized, including the ACP (BtrI), an ATP-dependent ligase (BtrJ), a pyridoxal phosphate-dependent decarboxylase (BtrK), and a two-component flavin-dependent monooxygenase system (BtrO and the previously unreported BtrV). The proposed biosynthetic pathway includes a γ-glutamylation of an ACP-derived γ-aminobutyrate intermediate, possibly a rare example of protective group chemistry in biosynthesis.

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