Reaction #57412

Reaction equation

ammonium hydroxide

ammonium formate

(3-hydroxy-adamantan-1-yl)-oxo-acetic acid

→

(S)-amino-(3-hydroxy-adamantan-1-yl)-acetic acid

Yield 105.5%

Conditions

Workup

1. 1
   workup.ADDITIONthe solution was added to the bottle
2. 2
   workup.ADDITIONcontaining the Escherichia coli
3. 3
   Extractionextract
4. 4
   TemperatureThe bottle was maintained at 400 on a shaker at 40 rpm
5. 5
   workup.ADDITIONConcentrated ammonium hydroxide was added periodically
6. 6
   Temperatureto maintain pH 8.0 After 38 hours

Procedure

A 266 ml solution was prepared containing ammonium formate (16.74 g, 0.2654 moles) and (3-hydroxy-adamantan-1-yl)-oxo-acetic acid (29.76 g, 0.1327 moles) and brought to pH 8.0 with 12.7 ml concentrated ammonium hydroxide. AND (372 mg, 0.561 mmoles) and dithiothreitol (81.8 mg, 0.530 mmoles) were added, then the solution was added to the bottle containing the Escherichia coli extract. The bottle was maintained at 400 on a shaker at 40 rpm. Concentrated ammonium hydroxide was added periodically to maintain pH 8.0 After 38 hours, the solution contained 31.5 grams (0.140 moles, 100% yield) (S)-amino-(3-hydroxy-adamantan-1-yl)-acetic acid as measured by HPLC analysis and no R-enantiomer of the amino acid.

Source