Journal
BIOCHEMISTRY
Volume 60, Issue 25, Pages 1947-1951Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.biochem.1c00257
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Funding
- National Science Foundation [1905336]
- Robert A. Welch Foundation [A0034]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1905336] Funding Source: National Science Foundation
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A chemoenzymatic synthesis method was described, which achieved yield enhancement by using different reducing agents and a fluorinated analogue. This synthesis route revealed the mechanism of the MqnD-catalyzed reaction.
MqnD catalyzes the conversion of cyclic dehypoxanthine futalosine (6) to 5,8-dihydroxy-2-naphthoic acid (7) and an uncharacterized product. This study describes a chemoenzymatic synthesis of 6. This synthesis achieved a 2-fold yield enhancement by using titanium(III) citrate as the reducing agent and another 5-fold yield enhancement using a fluorinated analogue of dehypoxanthine futalosine (5) that was converted to 6 by an ipso substitution mechanism. This synthetic route enabled the synthesis of 6 in sufficient quantity to identify the second reaction product and to determine that the MqnD-catalyzed reaction proceeds by a hemiacetal ring opening-tautomerization-retroaldol sequence.
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