Resolution of Non‐Protein Amino Acids via Carica papaya Lipase‐Catalyzed Enantioselective Transesterification.

Abstract

Resolution of Non-Protein Amino Acids via Carica papaya Lipase-Catalyzed Enantioselective Transesterification. -(MIYAZAWA*, T.; ONISHI, K.; MURASHIMA, T.; YAMADA, T.; TSAI, S.-W.; Tetrahedron: Asymmetry 16 (2005) 15, 2569-2573; Dep. Chem., Fac. Sci., Konan Univ., Higashinada, Kobe 658, Japan; Eng.) -Y. Steudel 51-170

Resolution of secondary alcohols via Carica papaya lipase-catalyzed enantioselective acylation

“…It was only more recently that Carica papaya lipase (CPL), stored in the crude papain produced from C. papaya latex, was employed for the kinetic resolutions of chiral acids such as 2-(4-chlorophenoxy)propanoic acid (Cheng and Tsai 2004) and profens (2-arylpropanoic acids) (Chen and Tsai 2005;Ng and Tsai 2005) via enantioselective esterification or hydrolysis. We also reported the CPL-mediated kinetic resolution of amino acids via the highly enantioselective alcoholysis of their N-benzyloxycarbonylated 2,2,2-trifluoroethyl esters (Miyazawa et al 2005). These successful results obtained with carboxylic acids prompted us to examine the capability of CPL for the resolution of alcohols via enantioselective acylation (transesterification) in organic milieu.…”

“…The crude papain (Sigma 5 g) was dissolved in distilled water (25 ml), centrifuged (10,000g, 12 min) at 4°C to collect the precipitate and lyophilized to afford the crude CPL (0.75 g) (Miyazawa et al 2005). A solution of an alcohol substrate (0.1 mmol) and vinyl alkanoate (0.4 mmol) in an organic solvent (0.8 ml) was stirred with the CPL preparation (10 mg) in a 1 ml screw-capped vessel at 45°C.…”

Carica papaya lipase-catalyzed transesterification resolution of secondary alcohols in organic solvents

“…Although industrial lipases are obtained mainly from animal and microbial sources, plant lipases from plant latex nowadays have become available in large quantities for utilization in lipids bioconversion (Cambon et al, 2006;Caro et al, 2000;Domínguez de María et al, 2006;Mukherjee and Gandhi, 2001;Palocci et al, 2003;Villeneuve, 2003). Recently, Carica papaya lipases stored in the crude papain produced from C. papaya latex were disclosed to have high enantioselectivity for the resolution of chiral acids such as 2-aryloxypropionic acids, 2-arylpropionic acids, N-benzyloxycarbonylated amino acids, and 2-fluoro-2-arylpropionic acids (Chen et al, 2005;Cheng and Tsai, 2007;Miyazawa et al, 2005;Tsai, 2005a,b, 2006a,b;Wang et al, 2006).…”

Enantioselective esterification of (R,S)-2-methylalkanoic acid with Carica papaya lipase in organic solvents

“…The hydrolytic resolution of (R,S)-arylpropionic thioesters with CPL, was also investigated in water-saturated organic solvents (Ng and Tsai 2005). CPL-catalyzed transesterification between the 2,2,2-trifluoroethyl esters of N-benzyloxycarbonylated DL-amino acids carrying aliphatic side chains, and methanol, in cyclohexane produced an enantioselectivity in excess of 200 (Miyazawa et al 2005). The price of crude papain is only about one-fourth to one-third price of the crude Candida rugosa lipase.…”