Homogentisic Acid → Phytyl diphosphate(3-)

HRID 29498Notes

Reaction equation

HRID 29498 reaction equation
C(O)(=O)CC1C(=CC=C(C=1)O)O.[CH3:13][C:14]1[C:19]([OH:20])=[CH:18][C:17]2[CH2:21][CH2:22][C@:23]([CH2:26][CH2:27][CH2:28][C@@H:29]([CH2:31][CH2:32][CH2:33][C@@H:34]([CH2:36][CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[CH3:35])[CH3:30])([CH3:25])[O:24][C:16]=2[C:15]=1[CH3:42].C[C@H](CCCC(C)C)CCC[C@H](CCC[C@@]1(C)OC2C=CC(O)=CC=2CC1)C.[OH:71][P:72]([OH:75])([OH:74])=[O:73]>>[O:73]([CH2:21]/[CH:22]=[C:23](/[CH2:26][CH2:27][CH2:28][C@@H:29]([CH2:31][CH2:32][CH2:33][C@@H:34]([CH2:36][CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[CH3:35])[CH3:30])\[CH3:25])[P:72]([O:75][P:72]([O-:74])([O-:73])=[O:71])(=[O:74])[O-:71].[CH3:42][C:15]1[CH:14]=[C:19]([OH:20])[CH:18]=[C:17]([CH2:21]/[CH:22]=[C:23](/[CH2:26][CH2:27][CH2:28][C@@H:29]([CH2:31][CH2:32][CH2:33][C@@H:34]([CH2:36][CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[CH3:35])[CH3:30])\[CH3:25])[C:16]=1[OH:24].[CH3:13][C:14]1[C:15]([CH3:42])=[C:16]([OH:24])[C:17]([CH2:21]/[CH:22]=[C:23](/[CH2:26][CH2:27][CH2:28][C@@H:29]([CH2:31][CH2:32][CH2:33][C@@H:34]([CH2:36][CH2:37][CH2:38][CH:39]([CH3:41])[CH3:40])[CH3:35])[CH3:30])\[CH3:25])=[CH:18][C:19]=1[OH:20]

Participants

7

Reactant 4

HCID 780Homogentisic Acid2×HCID 1004Phosphoric AcidHCID 92729(+)-gamma-TocopherolHCID 58866062Tocol, (2R)-

Product 3

HCID 71728454Phytyl diphosphate(3-)HCID 71768102PhytylplastoquinolHCID 717681352-Methyl-6-phytylquinol

Procedure

Homogentisic acid in 0.1% H3PO4 (specific radioactivity 40 Ci/mmol). Phytyl pyrophosphate was synthesized as described by Joo, et al. (1973) Can J. Biochem. 51:1527. 2-methyl-6-phytylquinol and 2,3-dimethyl-5-phytylquinol were synthesized as described by Soll, et al. (1980) Phytochemistry 19:215. Homogentisic acid, α, β, δ, and γ-tocopherol, and tocol, were purchased commercially.

Sources & evidence

ORD record
ord-094995bb8405496da2908e4229898680
Source dataset
uspto-grants-2008_09
Patent number
US07420101B2

Reaction notes

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