L-Tryptophan → (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

HRID 221212Notes

Reaction equation

HRID 221212 reaction equation
CC1C2NC3C(C=2C(C)=NC=1N)=CC=CC=3.[O:17]=[CH:18][C@@H:19]([C@H:21]([C@@H:23]([C@@H:25]([CH2:27][OH:28])[OH:26])[OH:24])[OH:22])[OH:20].N[C@H](C(O)=O)CC1C2C(=CC=CC=2)NC=1.OP([O-])(O)=O.[K+].[O-]S([O-])(=O)=O.[Mg+2].[Cl-].[Cl-].[Ca+2]>O>[O:17]=[CH:18][C@@H:19]([C@H:21]([C@@H:23]([C@@H:25]([CH2:27][OH:28])[OH:26])[OH:24])[OH:22])[OH:20]

Participants

7

Reactant 5

HCID 6305L-TryptophanHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516951Monobasic potassium phosphateHCID 5284359Calcium ChlorideHCID 131729326HCID 131729326, compound

Product 1

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trp-1+glucose medium, a minimal medium that has been used for increased production of tryptophan in E. coli cells (Zeman et al. Folia Microbiol. 35:200-4, 1990), was prepared as follows. To 700 mL nanopure water the following reagents were added: 2 g (NH4)2SO4, 13.6 g KH2PO4, 0.2 g MgSO4*7H20, 0.01 g CaCl2*2H20 and 0.5 mg FeSO4*7H20. The pH was adjusted to 7.0, the volume was increased to 850 mL, and the medium was autoclaved. A 50% glucose solution was prepared separately, and sterile-filtered. Forty mL was added to the base medium (850 mL) for a 1 L final volume.

Workup

  1. customcoli cells (Zeman et al. Folia Microbiol. 35:200-4, 1990), was prepared
  2. temperaturethe volume was increased to 850 mL
  3. filtrationsterile-filtered
  4. additionForty mL was added to the base medium (850 mL) for a 1 L final volume

Sources & evidence

ORD record
ord-6dae5b39046d4420be3d6869a3e44071
Source dataset
uspto-grants-2012_06
Patent number
US08206955B2

Reaction notes

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