Mechanistic studies on the biomimetic reduction of tetrahydroxynaphthalene, a key intermediate in melanin biosynthesis.
1,3,6,8-Tetrahydroxynaphthalene (T4HN) is an aromatic polyketide, serving as a general precursor of fungal melanin. Melanin biosynthesis involves two consecutive deoxygenations of T4HN, consisting of the reduction of a phenolic carbon followed by dehydration. The first reduction to produce scytalone was studied in a biomimetic reduction with sodium borohydride. The reduction required a strong alkaline condition, leading to the tautomerization of T4HN to a reactive species whose structure was clarified by NMR spectroscopy.
Ichinose
K
K
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Japan.
Ebizuka
Y
Y
Sankawa
U
U
D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008543:Melanins / Q000096:biosynthesis*; D018716:Molecular Mimicry; D009284:Naphthols / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D010084:Oxidation-Reduction
C121288:1,3,6,8-tetrahydroxynaphthalene; D008543:Melanins; D009284:Naphthols