Regioselective Enzymatic Acylation of Multi-hydroxyl Compounds in Organic Synthesis

  • Park, Hyun-Gyu (Department of Chemical and Biomolecular Engineering, Korea Advanced Institute of Science and Technology) ;
  • Do, Jin-Hwan (Department of Chemical and Biomolecular Engineering, Korea Advanced Institute of Science and Technology) ;
  • Chang, Ho-Nam (Department of Chemical and Biomolecular Engineerring, Korea Advanced Institute of Science and Technology)
  • Published : 2003.01.01

Abstract

With current developments in enzyme-catalyzed reactions and techniques available for rational redesign of natural biocatalysts, the enzymatic biosynthesis can become one of the most valuable Synthetic methods. Enzymatic regioselective catalysis in organic media has played a key role in pursuing asymmetric synthesis for active chiral compounds. Here, we shortly do-scribe some historical issues of the rapidly growing area, enzymatic catalysis in synthetic organic chemistry and then review researches that have been carried out in the regioselective enzymatic catalysis for the past two decades. An application of this technology to the modification of some potential target drug co m pound will be adios presented.

Keywords

References

  1. Chem. Eng. News v.76 Counting on chiral drugs Stinson,S.C.
  2. Tetrahedron v.42 Enzymes in organic synthesis Jones,J.B. https://doi.org/10.1016/S0040-4020(01)87306-3
  3. Enzymes in Synthetic Organic Chemistry Wong,C.H.;G.M.Whitesides
  4. Tetrahedron v.52 Enantioselective synthesis through enzymatic asymmetrzation Schoffers,E.;A.Golebiowski;C.R.Johnson https://doi.org/10.1016/S0040-4020(95)01021-1
  5. Curr. Opin. Drug. Discov. Dev. v.1 Biotransformations in the discovery and development of pharmaceuticals Zaks,A.;D.R.Dodds
  6. Angew. Chem. Int. Edn. Engl. v.39 Properties and Synthetic application of enzymes in organic solvents Carrea,G.;S.Riva https://doi.org/10.1002/1521-3773(20000703)39:13<2226::AID-ANIE2226>3.0.CO;2-L
  7. J. Ferment. Bioeng. v.81 Enzymatic resolution of racemic ibuprofen by lipase-catalyzed esterification reaction:Effects of water content and solid supports Kim,M.G.;S.B.Lee https://doi.org/10.1016/0922-338X(96)82221-5
  8. Biotechnol. Bioeng. v.73 Kinetic resolution of chiral amines ω-transaminase using an enzymemembrane reactor Shin,J.S.;B.G.Kim https://doi.org/10.1002/bit.1050
  9. J. Am. Chem. Soc. v.108 Facile enzymatic preparation of monoacylated sugars in pyridine Therisod,M.;A.M.Klibanov https://doi.org/10.1021/ja00278a053
  10. J. Am. Chem. Soc. v.109 Regioselective acylation of secondary hydroxyl groups in sugars catalyzed by lipases in organic solvents Therisod,M.;A.M.Klibanov https://doi.org/10.1021/ja00247a024
  11. J. Am. Chem. Soc. v.110 Protease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide Riva,S.;J.Chopineau;A.P.G.Kieboom;A.M.Klibanov https://doi.org/10.1021/ja00210a045
  12. J. Am. Chem. Soc. v.110 Lipase-catalyzed irreversible transesterifications using enol esters as acylating reagents:Preparative enantio-and regioselective syntheses of alcohols, glycerol derivatives, sugars, and organometallics Wang,Y.F.;J.J.Lalonde;M.Momongan;D.E.Bergbreiter;C.H.Wong https://doi.org/10.1021/ja00229a041
  13. J. Org. Chem. v.53 Enzymes in carbohydrate synthesis:Lipase catalyzed selective acylation and deacylation of furanose and pyranose derivatives Hennen,W.J.;H.M.Sweers;Y.F.Wang;C.H.Wong https://doi.org/10.1021/jo00256a008
  14. J. Chem. Soc. Perkin Trans. v.Ⅰ Enzymatic synthesis of various 1'-O-sucrose and 1-O- fructose esters Carrea,G.;S.Riva;F.Secundo;B.Danieli
  15. Carbohyd. Res. v.252 Towards the selective acylation of secondary hydroxyl groups of enzyme-catalyzed process Pulido,R.;V.Gotor
  16. J. Mol. Catal. B-Enzym. v.6 Lipase-catalyzed solid-phase synthesis of sugar esters. Influence of immobilization on productivity and stability of the enzyme Cao,L.;U.T.Bornscheuer;R.D.Schmid https://doi.org/10.1016/S1381-1177(98)00083-6
  17. Science v.224 Enzymatic catalysis in organic media at 100°C Zaks,A.;A.M.Klibanov https://doi.org/10.1126/science.6729453
  18. Proc. Natl. Acad. Sci. USA v.82 Enzyme catalyzed processes in organic solvents Zaks,A.;A.M.Klibanov https://doi.org/10.1073/pnas.82.10.3192
  19. Am. Chem. J. v.24 Concerining lipase, the fat-splitting enzyme, and the reversibility of its action Kastle,J.H.;A.S.Lovenhart
  20. $\"{U}$ber die Esterasewirkung Ⅲ Biochem. Z. v.258 Sym,E.A.
  21. Enzymologia v.258 Eine Methode der Enzymatischen Estersynthesen Sym,E.A.
  22. US Patent 4,275,081 Fat process and composition Coleman,M.H.;A.R.Macrae
  23. US Patent 4,268,527 Method for producing cacao butter substitute Matsuo,T;N.Sawamura;Y.Hashimoto;W.Hashida
  24. Trends Biotechnol. v.17 Why did biocatalysis in organic media not take off in the 1930s? Halling,P.;L.Kvittingen https://doi.org/10.1016/S0167-7799(99)01331-1
  25. Trends Biotechnol. v.18 Answering the question:Why did biocatalysis in organic media not take off in the 1930s? Klibanov,A.M. https://doi.org/10.1016/S0167-7799(99)01404-3
  26. Biotechnol. Bioeng. v.72 Chemoenzymatic synthesis of a sucrose-containing aromatic polymers Park,H.G.;H.N.Chang;J.S.Dordick https://doi.org/10.1002/1097-0290(20010305)72:5<541::AID-BIT1018>3.0.CO;2-C
  27. Biotechnol. Bioeng. v.37 Enzymatic synthesis of a sucrose-containing linear polyester in nearly anhydrous organic media Patil,D.R.;D.G.Rethwisch;J.S.Dordick https://doi.org/10.1002/bit.260370706
  28. Biotechnol. Lett. v.22 Enzymatic regioselective synthesis of sucrose acylate esters Park,H.G.;H.N.Chang https://doi.org/10.1023/A:1005608527178
  29. Biotechnol. Bioeng. v.45 Controlling enzyme-catalyzed regioselectivity in sugar ester synthesis Rich,J.O.;B.A.Bedell;J.S.Dordick https://doi.org/10.1002/bit.260450507
  30. Biotechnol. Bioeng. v.31 Production of biosurfactants from sugar alcohols and vegetable oils catalyzed by lipase in a nonaqueous medium Chopineau,J.;F.D.McCafferty;M.Therisod;A.M.Klibanov https://doi.org/10.1002/bit.260310305
  31. Chemtech. Chemical and biochemical catalysis to make swellable polymers Dordick,J.S.;R.J.Linhardt;D.G.Rethwisch
  32. Biotechnol. Bioeng. v.70 Enzymecatalyzed synthesis of sugar-containing monomers and linear polymers Park,O.J.;D.Y.Kim;J.S.Dordick https://doi.org/10.1002/1097-0290(20001020)70:2<208::AID-BIT10>3.0.CO;2-0
  33. Ann. NY. Acad. Sci. v.864 Enzymatic synthesis of phenol-sucrose copolymer using peroxidase in organic solvent and its reaction optimization Joo,H.;Y.J.Yoo https://doi.org/10.1111/j.1749-6632.1998.tb10389.x
  34. Ann. NY. Acad. Sci. v.864 Enzymatic modification of natural compounds with pharmacological properties Riva,S.;D.Monti;M.Luisetti;B.Danieli https://doi.org/10.1111/j.1749-6632.1998.tb10289.x
  35. J. Org. Chem. v.60 Regioselective enzyme-mediated acylation of polyhydroxy natural compounds:a remarkable, highly efficient preparation of 6'-O-acetyl and 6'-O-carboxy-acetyl ginsenoside Rg₁ Danieli,B.;M.Luisetti;S.Riva;A.Bertinotti;E.Ragg;L.Scaglioni;E.Bombardelli https://doi.org/10.1021/jo00117a012
  36. J. Org. Chem. v.64 Enzyme-mediated regioselective acylations of sophorolipids Bisht,K.S.;R.A.Gross;D.L.Kaplan https://doi.org/10.1021/jo981497m
  37. J. Am. Chem. Soc. v.119 Synthesis of water soluble Paclitaxel derivatives by enzymatic acylation Khmelnitski,Y.L.;C.Budde;J.M.Arnold;A.Usyatinsky;D.S.Clark;J.S.Dordick https://doi.org/10.1021/ja973103z
  38. Carbohyd. Res. v.299 Synthesis of α-tocopheryl oligosaccharides Lahmann,M.;J.Thiem https://doi.org/10.1016/S0008-6215(96)00331-X
  39. US Patent 5,824,689 Quinoline compound extracted from scolopendra subspinipes, and derivatives thereof Lee,H.S.;Y.J.Park;M.H.Kim;S.S.Moon;N.S.Cho;J.H.Shin;Y.W.Suh;J.O.Lee
  40. Nature v.409 Enzymes for chemical synthesis Koeller,K.M.;C.H.Wong https://doi.org/10.1038/35051706