Hydrochloric Acid → Monatin

HRID 1160784Notes

Reaction equation

HRID 1160784 reaction equation
N1C2C(=CC=CC=2)C(CC(=O)C(O)=O)=C1.[OH-].[Na+].Cl.C([O-])(=O)C(C)=O.[Na+].N[C@@H](C(O)=O)C.CC1C(O)=C(C=O)C(COP(O)(O)=O)=CN=1.[CH:48]1[CH:53]=[C:52]2[C:54]([CH2:57][C@@:58]([OH:68])([C:65]([OH:67])=[O:66])[CH2:59][C@@H:60]([NH2:64])[C:61]([OH:63])=[O:62])=[CH:55][NH:56][C:51]2=[CH:50][CH:49]=1>O>[CH:48]1[CH:53]=[C:52]2[C:54]([CH2:57][C@@:58]([OH:68])([C:65]([OH:67])=[O:66])[CH2:59][C@H:60]([NH2:64])[C:61]([OH:63])=[O:62])=[CH:55][NH:56][C:51]2=[CH:50][CH:49]=1

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 803Indole-3-pyruvic acidHCID 1051Pyridoxal 5'-phosphateHCID 14798Sodium HydroxideHCID 71080D-AlanineHCID 9814579D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)-HCID 23662274Sodium pyruvate

Product 1

HCID 9860847Monatin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.0 g of indole-3-pyruvic acid was suspended in 100 ml of water, which was dissolved by addition of 2N sodium hydroxide aqueous solution and adjusted to pH 12. Then, the solution was adjusted to pH 9 by addition of 1N hydrochloric acid, and then sodium pyruvate (8.12 g) and the solution of trans-L-hydroxyproline/zinc (II) complex (22 ml) were added. The mixture was stirred at room temperature for 4 hours, and the cross-aldol reaction was performed. To 25 ml of the obtained reaction mixture, D-Ala (1.8 g) and pyridoxal-5′-phosphate (1 mg) were added, and then 0.5 g of BMDAT-expressing E. coli or S243N/A182S mutant BMDAT-expressing E. coli was added in suspension to carry out amination reaction at 33° C. for 24 hours. By HPLC analysis of the reaction mixture with appropriate dilution, it was confirmed to genarate (2R,4R)-monatin or (2R,4S)-monatin as shown in Table 4. Incidentally, the BMDAT-expressing E. coli and S243N/A182S mutant BMDAT-expressing E. coli used for the amination reaction were prepared according to the method described in the following Reference Example.

Workup

  1. customthe cross-aldol reaction
  2. additionwere added
  3. additioncoli was added in suspension
  4. customto carry out amination reaction at 33° C. for 24 hours
  5. customcoli used for the amination reaction
  6. customwere prepared

Sources & evidence

ORD record
ord-3d537ffd6cb54bb4b71e7e573b0692a1
Source dataset
uspto-grants-2010_10
Patent number
US07816541B2

Reaction notes

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