2021
DOI: 10.1021/acs.biochem.1c00257
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Menaquinone Biosynthesis: The Mechanism of 5,8-Dihydroxy-2-naphthoate Synthase (MqnD)

Abstract: 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 suffici… Show more

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“…An additional compound worth mentioning is dehypoxanthine futalosine (tR = 7.08, with m/z 296.0897, Table 1). It is a biosynthetic intermediate in the menaquinone (Vitamin K) biosynthesis (Manion-Sommerhalter et al, 2021), first reported as a potential honey constituent.…”
Section: Anama Honey Secondary Metabolites-chemical Markersmentioning
confidence: 99%
“…An additional compound worth mentioning is dehypoxanthine futalosine (tR = 7.08, with m/z 296.0897, Table 1). It is a biosynthetic intermediate in the menaquinone (Vitamin K) biosynthesis (Manion-Sommerhalter et al, 2021), first reported as a potential honey constituent.…”
Section: Anama Honey Secondary Metabolites-chemical Markersmentioning
confidence: 99%