Microbial asymmetric hydrolysis ofN-acetyl-1-methyl-3-phenylpropylamine to optically active 1-methyl-3-phenylpropylamine

✍ Scribed by Sakayu Shimizu; Jun Ogawa; Hideaki Yamada

• Publisher: Springer
• Year: 1992
• Tongue: English
• Weight: 425 KB
• Volume: 37
• Category: Article
• ISSN: 1432-0614
• DOI: 10.1007/bf00178164

✦ Synopsis

The asymmetric hydrolysis o f N-acetyl-l-methyl-3-phenylpropylamine (MPAc) by microorganisms was investigated. Various bacteria belonging to the genera Bacillus, Agrobacterium, Corynebacterium, Arthrobacter, Brevibacterium, Cellulomonas, Acinetobacter, Nocardia and Rhodococcus showed this hydrolysing activity and yielded (S)-l-methyl-3-phenylpropylamine (MPPA). Using washed cells o f N. erythropolis IAM 1440, 15.1 m g / m l o f ( S ) -M P P A was formed, with a 38.8°7o conversion yield and high stereoselectivity (97.9070 enantiomeric excess), in an organic solvent-water diphase system. The same (S)-amine and (S)-l-phenylethylamine were also produced in good yields f r o m the valeryl and isovaleryl derivatives o f M P P A , and Nacetyl-1-phenylethylamine, respectively.