2023
DOI: 10.1021/jacs.3c06354
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Biosynthetic Origin of the Octose Core and Its Mechanism of Assembly during Apramycin Biosynthesis

Po-Hsun Fan,
Shusuke Sato,
Yu-Cheng Yeh
et al.

Abstract: Apramycin is an aminoglycoside antibiotic isolated from Streptoalloteichus tenebrarius and S. hindustanus that has found clinical use in veterinary medicine. The apramycin structure is notable for its atypical eight-carbon bicyclic dialdose (octose) moiety. While the apramycin biosynthetic gene cluster (apr) has been identified and several of the encoded genes functionally characterized, how the octose core itself is assembled has remained elusive. Nevertheless, recent gene deletion studies have hinted at an N… Show more

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Cited by 6 publications
(14 citation statements)
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“…In this study, the functions of the remaining uncharacterized enzymes in the apr cluster were elucidated, thereby establishing the complete biosynthetic pathway for apramycin (see Figures and ). The 4-amino-4-deoxy- d -glucose moiety is derived from G6P ( 4 ), which is consistent with previous results indicating the incorporation of intact glucose into the second sugar moiety of apramycin . Equilibration of G6P ( 4 ) with β-G1P ( 13 ) is catalyzed by AprJ and biased toward G6P ( K eq = 0.031).…”
Section: Discussionsupporting
confidence: 91%
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“…In this study, the functions of the remaining uncharacterized enzymes in the apr cluster were elucidated, thereby establishing the complete biosynthetic pathway for apramycin (see Figures and ). The 4-amino-4-deoxy- d -glucose moiety is derived from G6P ( 4 ), which is consistent with previous results indicating the incorporation of intact glucose into the second sugar moiety of apramycin . Equilibration of G6P ( 4 ) with β-G1P ( 13 ) is catalyzed by AprJ and biased toward G6P ( K eq = 0.031).…”
Section: Discussionsupporting
confidence: 91%
“…d -Glucose ( 14 ), G6P ( 4 ), α- d -glucose 1-phosphate (α-G1P, 16 ), UDP-α- d -glucose ( 17 ), and α,α-trehalose ( 18 ) were tested as candidate sugar donors (Figure A). After overnight incubation, the 5-phosphate group was removed by treatment with AprZ prior to derivatization with 1-fluoro-2,4-dinitrobenzene (DNFB) under basic conditions . Only G6P ( 4 ) was almost completely consumed, yielding a product with m / z 1203.2633 in negative mode upon liquid chromatography with mass spectrometric analysis (LC–MS), which was consistent with the pseudomolecular ion of the tetra-dinitrophenyl (DNP) derivative of 2 (calcd.…”
Section: Resultsmentioning
confidence: 82%
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