Synthesis of optically active α-methyl amino acids utilizing biotransformation as a key step

ORGN 269

Masanobu Yatagai, masanobu_yatagai@ajinomoto.com, Takayuki Hamada, Hiroyuki Nozaki, Shinji Kuroda, Kenzo Yokozeki, and Kunisuke Izawa. AminoScience Laboratories, Ajinomoto Co., Inc, 1-1 Suzuki-cho, Kawasaki, 210-8681, Japan
Optically active α-methyl α-amino acids are important building blocks for the synthesis of peptide, pharmaceutical and agrochemical compounds, in which the quaternary carbons show the effect on their conformations and biological activities. A new synthetic method for α-methyl-L-cysteine was realized by enzymatic resolution of racemic 2,4-dimethyl-4-methoxycarbonylthiazoline which can be derived from chloroacetone in 4 steps. Optically active 2,4-dimethyl-4-methoxycarbonylthiazoline was alternatively derived from α-methyl-L-serine as a starting material. In this presentation, a new enzymatic synthesis of α-methyl-L-serine will be also referred.