Chloramphenicol → L-Phenylalanine

HRID 1027352Notes

Reaction equation

HRID 1027352 reaction equation
[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7](O)=[CH:6][CH:5]=1.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[NH4+].[Cl-].C1C([C@@H](O)[C@H](NC(C(Cl)Cl)=O)CO)=CC=C([N+]([O-])=O)C=1.C1[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](N)[C@H]2O)[C@@H]1N>C1N(CCCS(O)(=O)=O)CCOC1>[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 5959ChloramphenicolHCID 6032KanamycinHCID 6057L-TyrosineHCID 25517Ammonium ChlorideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 6140L-Phenylalanine

Reagents, catalysts & solvents 1

HCID 70807MopsSolvent

Procedure

L-tyrosine production experiments were performed at 37° C. with 225 rpm orbital shaking in 50 ml MOPS minimal medium (Teknova) (Neidhardt, Bloch et al. 1974) cultures supplemented with 5 g/l glucose and an additional 4 g/l NH4Cl. All liquid cultivations were conducted in at least triplicates. When appropriate, antibiotics were added in the following concentrations: 34 μg/ml chloramphenicol for maintenance of pHACM-derived plasmids and 20 μg/ml kanamycin for maintenance of pZE-derived plasmids. L-phenylalanine auxotrophic (ΔpheA) cultures were additionally provided with L-phenylalanine (Sigma) at a concentration of 0.35 mM.

Workup

  1. customwere performed at 37° C. with 225 rpm
  2. additionWhen appropriate, antibiotics were added in the following concentrations

Sources & evidence

ORD record
ord-afa5e19ef9954e55a90885585ba46ecf
Source dataset
uspto-grants-2014_05
Patent number
US08735132B2

Reaction notes

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