Reaction #1797503

ord-1f061e6c70e247289b3a99639d848c94

Reaction equation

NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
NAD
O=C[C@H](O)[C@H](O)COP(=O)(O)O
D-Erythrose 4-phosphate
CC(=O)C(=O)[O-].[Na+]
sodium pyruvate
→
O=C(O)C1=CC(=O)[C@@H](O)[C@H](O)C1
3-Dehydroshikimate
Yield 90.0%

Reactants

NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
NAD
O=C[C@H](O)[C@H](O)COP(=O)(O)O
D-Erythrose 4-phosphate
CC(=O)C(=O)[O-].[Na+]
sodium pyruvate
—
CoCl2

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherProtein is subsequently removed by ultrafiltration

Procedure

D-Erythrose 4-phosphate (0.45 mL, 12 mM, pH 7.0), sodium pyruvate (0.054 mL, 100 mM, pH 7.0), CoCl2 (0.027 mL, 10 mM), NAD (0.054 mL, 1 mM), DHQ synthase (2 units) and DHQ dehydratase (2 units) are incubated with KDPGal aldolase (100 units) from E. coli at room temperature for 2 h. Protein is subsequently removed by ultrafiltration using Millipore PM-10 membrane. 3-Dehydroshikimate was formed in 90% yield, as determined by 1H NMR analysis.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07790431B2uspto-grants-2010_09