Resolution of 2-phenoxy-1-propanols through the enantioselective acylation mediated by Achromobacter sp. lipase as biocatalyst

Biocatalysis and Biotransformation

Volumn 24, Issue 3, 2006, Pages 231-235

  Miyazawa, Toshifumi ^a   Yukawa, Tomoyuki ^a   Yamada, Takashi ^a  

^a KONAN UNIVERSITY   (Japan)

Author keywords

2 phenoxy 1 propanols; Achromobacter sp. lipase; Acyl donor; Enantioselective acylation; Enzymatic resolution

Indexed keywords

ACYLATION; ALCOHOLS; BENZENE; ETHERS; SOLVENTS;

ACHROMOBACTER SP. LIPASE; ACYL DONOR; ENANTIOSELECTIVE ACYLATION; ENZYMATIC RESOLUTION; PHENOXY PROPANOLS;

BIOCATALYSTS;

2 (4 CHLOROPHENOXY) 1 PROPANOL; 2 PHENOXY 1 PROPANOL DERIVATIVE; ALCOHOL; ALCOHOL DERIVATIVE; ALKANOIC ACID; BUTYRIC ACID DERIVATIVE; DIISOPROPYL ETHER; ORGANIC SOLVENT; OXYGEN; PROPANOL; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ACHROMOBACTER; ACYLATION; ARTICLE; BIOCATALYST; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOMER; ENANTIOSELECTIVITY; NONHUMAN; RACEMIC MIXTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

ACHROMOBACTER SP.;

EID: 33748369661     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.1080/10242420600654708     Document Type: Article

References (18)

1. Berger, B and Rabiller, CG and Königsberger, K and Faber, K and Griengl, H. (1990) Enzymatic acylation using acid anhydrides: Crucial removal of acid Tetrahedron: Asymmetry, 1, pp. 541-546.
2. Bornscheuer, UT and Kazlauskas, RJ. (2005) Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations 2nd edn. Wiley-VHC: Weinheim.
3. Chen, C-S and Fujimoto, Y and Girdaukas, G and Sih, CJ. (1982) Quantitative analyses of biochemical kinetic resolutions of enantiomers J Am Chem Soc, 104, pp. 7294-7299.
4. Dirlam, NL and Moore, BS and Urban, FJ. (1987) Novel synthesis of the aldose reductase inhibitor sorbinil via amidoalkylation, intramolecular oxazolidin-5-one alkylation, and chymotrypsin resolution J Org Chem, 52, pp. 3587-3591.
5. Faber K. 2004. Biotransformations in Organic Chemistry, 5th edn. Springer-Verlag: Berlin. pp 94-123 and 344-366.
6. Gais, HJ and Theil, F. (2002) Hydrolysis and formation of C-O bonds. In Enzyme Catalysis in Organic Synthesis. (pp. 335). Weinheim: Wiley-VHC.
7. Itoh, T and Uzu, A and Kanda, N and Takagi, Y. (1996) Preparation of 3-alkyl-4-hydroxy-2-butenyl acetate through highly regioselective lipase-catalyzed hydrolysis of corresponding diacetates Tetrahedron Lett, 37, pp. 91-92.
8. Kazlauskas, RJ and Weissfloch, ANE and Rappaport, AT and Cuccia, LA. (1991) A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase, lipase from Pseudomonas cepacia, and lipase from Candida rugosa J Org Chem, 56, pp. 2656-2665.
9. Klibanov, AM. (1986) Enzymes that work in organic solvents Chemtech, 16, pp. 354-359.
10. Koskinen AMP, Klibanov AM, eds1996. Enzymatic Reactions in Organic Media. Blackie A & P: Glasgow.
11. Laane, C and Boeren, S and Vos, K. and Veeger, C. (1987) Rules for optimization of biocatalysis in organic solvents Biotechnol Bioeng, 30, pp. 81-87.
12. Miyazawa, T and Kurita, S and Ueji, S. and Yamada, T. (2000) Resolution of mandelic acids by lipase-catalyzed transesterifications in organic media Biocatal Biotrans, 17, pp. 459-473.
13. Miyazawa, T and Yukawa, T and Koshiba, T and Sakamoto, H and Ueji, S and Yanagihara, R and Yamada, T. (2001a) Resolution of 2-aryloxy-1-propanols via lipase-catalyzed enantioselective acylation in organic media Tetrahedron: Asymmetry, 12, pp. 1595-1602.
14. Miyazawa, T and Yukawa, T and Koshiba, T and Ueji, S and Yanagihara, R and Yamada, T. (2001b) Enzymatic resolution of 2-phenoxy-1-propanols through the enantioselective acylation mediated by Achromobacter sp. lipase Biotechnol Lett, 23, pp. 1547-1550.
15. OkamotoT, UejiS. 1999. Drastic enhancement of the enantioselectivity of lipase-catalysed esterification in organic solvents by the addition of metal ions. J Chem Soc Chem Commun 939-940.
16. Weissfloch, ANE and Kazlauskas, RJ. (1995) Enantiopreference of lipase from Pseudomonas cepacia toward primary alcohols J Org Chem, 60, pp. 6959-6969.
17. Wimmer, Z and Saman, D and Francke, W. (1994) Novel juvenoids of the 2-(4-hydroxybenzyl)cyclohexan-1-one series Helv Chim Acta, 77, pp. 502-508.
18. Yasufuku, Y and Ueji, S. (1997) High temperature-induced high enantioselectivity of lipase for esterification of 2-phenoxypropionic acids in organic solvent Bioorg Chem, 25, pp. 88-99.