3,4-Dihydro-3,6,8-trihydoroxy-1(2H)-napthalenone → 1,3,6,8-Naphthalenetetrol

HRID 1895829

Reaction equation

HRID 1895829 reaction equation
[CH2:1]1[C:11]2[C:6](=[C:7]([OH:13])[CH:8]=[C:9]([OH:12])[CH:10]=2)[C:4](=[O:5])[CH2:3][C@H:2]1[OH:14].OC1C2C(=CC=CC=2O)C=C(O)C=1.C(SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2)[C@H](O)[C@@H]1OP(O)(O)=O)(=O)CC(O)=O>>[OH:5][C:4]1[C:6]2[C:11](=[CH:10][C:9]([OH:12])=[CH:8][C:7]=2[OH:13])[CH:1]=[C:2]([OH:14])[CH:3]=1

Participants

4

Reactant 3

HCID 4393093,4-Dihydro-3,6,8-trihydoroxy-1(2H)-napthalenoneHCID 4394281,3,8-TrihydroxynaphthaleneHCID 644066Malonyl CoA

Product 1

HCID 4402021,3,6,8-Naphthalenetetrol

Procedure

Biosynthesis of DHN melanin is synthesized by a polyketide pathway, through the genes encoding Polyketide synthase (PKS), Scytalone dehydratase (SCD), and 1,3,8-trihydroxynaphthalene reductase (THN). It started with a PKS using malonyl-CoA as a substrate to produce 1,3,6,8-tetrahydroxynaphthalene, 1,3,6,8-THN (Fujii et al., 2000), followed by reducatse catalysis to produce scytalone, dehydration by SCD to yield 1,3,8-trihydroxynaphthalene (1,3,8-THN), reduction by THN to yield vermelone, dehydration to produce melanin precursor 1,8-dihydroxynaphthalene (1,8-DHN), and then oxidation and polymerization to yield melanin.

Sources & evidence

ORD record
ord-ce00f41e87b947328bc4cb0434182911
Source dataset
uspto-grants-2013_08
Patent number
US08518393B2

Linked notes

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