Ammonia → Mandelonitrile

HRID 1588468Notes

Reaction equation

HRID 1588468 reaction equation
[C:1](O)(=O)[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[NH3:12].C1C=CC([C@@H](O)C(O)=O)=CC=1>>[C:1](#[N:12])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1292Mandelic AcidHCID 11914(-)-Mandelic acid

Product 1

HCID 10758Mandelonitrile

Procedure

Microbial cells harvested from the plate culture were washed with a 50 mM phosphoric acid buffer solution (pH=7.5) and suspended in 10 ml of the same buffer solution to prepare a resting cell suspension at a cell concentration having an optical density at 630 nm (OD630 ) of from 1 to 50. To the cell suspension was added mandelonitrile to a concentration of 0.2 w/v %, and the system was allowed to react at 30° C. for 16 to 24 hours. Analysis of the reaction mixture by liquid chromatography (Shiseido ODS column); revealed the production of mandelic acid and ammonia. Further, analysis by means of a chiral cell for optical resolution("CHIRALPAK WH" column) revealed that the produced R(-)-mandelic acid had a high optical purity.

Workup

  1. washwere washed with a 50 mM phosphoric acid buffer solution (pH=7.5)
  2. customto prepare a resting cell suspension
  3. concentrationat a cell concentration
  4. additionTo the cell suspension was added mandelonitrile to a concentration of 0.2 w/v %, and the system
  5. customto react at 30° C. for 16 to 24 hours

Sources & evidence

ORD record
ord-51156faea78d41338f3c032f15c36639
Source dataset
uspto-grants-1993_06
Patent number
US05223416

Reaction notes

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