Stereoselective lipases from Burkholderia sp., cloning and their application to preparation of methyl (R)-N-(2,6-dimethylphenyl)alaninate, a key intermediate for (R)-Metalaxyl.
Two microbial strains (referred to as MC 16-3 and 99-2-1) that produce extracellular lipases were isolated from soil samples and identified as Burkholderia species. The lipases were partially purified by isopropyl alcohol precipitation and gave molecular weight of 33kDa. The lipases were characterized in terms of stereoselectivity with racemic methoxyethyl (R,S)-N-(2,6-dimethylphenyl)alaninate and the genes encoding the proteins have been identified by homology alignment of lipases reported belonging to I.2 subfamily and their complete DNA sequences were determined. The lipases will be useful for the preparation of methyl (R)-N-(2,6-dimethylphenyl)alaninate, a key intermediate for the synthesis of (R)-Metalaxyl, which is one of the best-selling fungicides.
Park
Oh-Jin
OJ
LG Chem, Ltd/Research Park, Corporate R&D 104-1, Moonji-dong, Yusung-gu, Daejon 305-380, Republic of Korea. parko@lgchem.com
Lee
Sang-Hyun
SH
D000409:Alanine / Q000031:analogs & derivatives* / Q000096:biosynthesis; D000595:Amino Acid Sequence; D001483:Base Sequence; D001709:Biotechnology; D019117:Burkholderia / Q000201:enzymology* / Q000235:genetics; D003001:Cloning, Molecular; D004269:DNA, Bacterial / Q000235:genetics; D005659:Fungicides, Industrial / Q000378:metabolism*; D005798:Genes, Bacterial; D008049:Lipase / Q000235:genetics / Q000302:isolation & purification / Q000378:metabolism*; D008969:Molecular Sequence Data; D017386:Sequence Homology, Amino Acid
D004269:DNA, Bacterial; D005659:Fungicides, Industrial; C028175:metalaxyl; D008049:Lipase; D000409:Alanine