Abstract
The following results were obtained: (1) A commercial protease preparation gave the best enantioselective hydrolysis of N-acetyl-dl-methionine methyl ester (N-Ac-dl-MetOMe) to produce N-Ac-l-Met with >99% e.e. (2) Solid NaHCO3 prevented chemical hydrolysis of N-Ac-dl-MetOMe. (3) N-Ac-l-Met was produced more efficiently when the pH was maintained at 7 with a mild base. (4) Crystalline N-Ac-l-Met and d-Met were simultaneously obtained with >99% e.e. in 45 and 36% yield, respectively, from the reaction mixture.
Similar content being viewed by others
References
Bergen TJV, Hedstrand DM, Kruizinga WH, Kellogg RM (1979) Hydride transfer from 1,4-dihydropiridines to sp3-hybridized carbon in sulfonium salts and activated halides. J. Org. Chem. 44: 4953–4962.
Chibata I, Ishikawa T, Yamada S (1957) Studies on amino acids. VII. Bull. Agr. Chem. Soc. Japan 21: 300–303.
Compagnone SR, Rapoport H (1986) Chirospecific synthesis of (+)-pilocarpine. J. Org. Chem., 51: 1713–1719.
Mor A, Delfour A, Nicolas P (1991) Identification of a D-alanine-containing polypeptide precursor for the peptide opioid, dermorphin. J. Biol. Chem. 266: 6264–6270.
Moriguchi M, Ideta K (1988) Production of D-aminoacylase from Alcaligenes denitrificans subsp. xylosoxydans MI-4. Appl. Environ. Microbiol. 54: 2767–2770.
Stauffer CE (1976) Process for producing N-acyl-L-methionine. United States patent 3963573.
Takahashi E, Furui M, Seko H, Shibatani T (1997) Appl. Microbiol. Biotechnol. 47: 173–179.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Furutani, T., Furui, M. Resolution of N-acetyl-DL-methionine methyl ester by protease-catalyzed hydrolysis with mild base as the pH control reagent. Biotechnology Letters 21, 1101–1105 (1999). https://doi.org/10.1023/A:1005622126036
Issue Date:
DOI: https://doi.org/10.1023/A:1005622126036