methyl alpha-D-glucopyranoside → Shikimic Acid
Reaction equation
[CH2:1]1[C@@H:6]([OH:7])[C@@H:5]([OH:8])[C@H:4]([OH:9])[CH2:3][C@@:2]1([C:11]([OH:13])=[O:12])O.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.O(C)[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O>>[CH2:3]1[C:2]([C:11]([OH:13])=[O:12])=[CH:1][C@@H:6]([OH:7])[C@@H:5]([OH:8])[C@@H:4]1[OH:9]Participants
Procedure
An alternative to increasing Kc in order to suppress quinic acid formation was addition of a non-hydrolyzable glucose analog to the fermentation broth. Methyl α-D-glucopyranoside (MαDG) was added to the fermentation medium at the time of inoculation and the fermentation was then run without further adjustment. Addition of 1 mM MαDG to the fermentation of SP1.1/pKD12.112 resulted in the synthesis of 40.3 g/L of shikimic acid (Table 3). Quinic acid was not detected. Although several concentrations were examined, 1 mM MαDG was the minimum concentration that afforded complete suppression of quinic acid formation. Addition of MαDG to SP2.1/pKD12.112 cultures also resulted in quinic acid suppression. After 48 h of culturing in the presence of 0.5 mM MαDG, SP2.1/pKD12.112 (Table 3) synthesized 39.6 g/L of shikimic acid and 4.1 g/L of quinic acid, resulting in a molar ratio 11. Higher concentrations of MαDG showed no further improvement in quinic acid suppression.
Workup
- temperatureAn alternative to increasing Kc in order
Sources & evidence
- ORD record
- ord-b0fef94345294dd592801d038bc7102f
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06613552B1
Reaction notes
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