[KSCI] Korea Science Citation Index Service

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)

Publication Information

Biotechnology and Bioprocess Engineering:BBE / v.8, no.1, 2003 , pp. 1-8 More about this Journal

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

enzymatic synthesis; regioselective synthesis; Sugar acylation; glycoside; drug modification; jineol;

Citations & Related Records

Times Cited By Web Of Science : 27 (Related Records In Web of Science)
Times Cited By SCOPUS : 12

Reference
Cited By SCOPUS

1	Enzymatic modification of natural compounds with pharmacological properties / [ Riva,S.;D.Monti;M.Luisetti;B.Danieli ] / Ann. NY. Acad. Sci. DOI
2	Enzymecatalyzed synthesis of sugar-containing monomers and linear polymers / [ Park,O.J.;D.Y.Kim;J.S.Dordick ] / Biotechnol. Bioeng. DOI ScienceOn
3	Enzymatic synthesis of various 1'-O-sucrose and 1-O- fructose esters / [ Carrea,G.;S.Riva;F.Secundo;B.Danieli ] / J. Chem. Soc. Perkin Trans.
4	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 ] / J. Am. Chem. Soc. DOI ScienceOn
5	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 ] / US Patent 5,824,689
6	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 ] / J. Am. Chem. Soc. DOI
7	Enzymatic regioselective synthesis of sucrose acylate esters / [ Park,H.G.;H.N.Chang ] / Biotechnol. Lett. DOI ScienceOn
8	Enzymatic synthesis of phenol-sucrose copolymer using peroxidase in organic solvent and its reaction optimization / [ Joo,H.;Y.J.Yoo ] / Ann. NY. Acad. Sci. DOI ScienceOn
9	Enantioselective synthesis through enzymatic asymmetrzation / [ Schoffers,E.;A.Golebiowski;C.R.Johnson ] / Tetrahedron DOI ScienceOn
10	/ [ Sym,E.A. ] / <TEX>$\"{U}$</TEX>ber die Esterasewirkung Ⅲ Biochem. Z.
11	Answering the question:Why did biocatalysis in organic media not take off in the 1930s? / [ Klibanov,A.M. ] / Trends Biotechnol. DOI ScienceOn
12	Why did biocatalysis in organic media not take off in the 1930s? / [ Halling,P.;L.Kvittingen ] / Trends Biotechnol. DOI ScienceOn
13	Properties and Synthetic application of enzymes in organic solvents / [ Carrea,G.;S.Riva ] / Angew. Chem. Int. Edn. Engl. DOI ScienceOn
14	Facile enzymatic preparation of monoacylated sugars in pyridine / [ Therisod,M.;A.M.Klibanov ] / J. Am. Chem. Soc. DOI
15	Fat process and composition / [ Coleman,M.H.;A.R.Macrae ] / US Patent 4,275,081
16	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 ] / J. Org. Chem. DOI ScienceOn
17	Synthesis of α-tocopheryl oligosaccharides / [ Lahmann,M.;J.Thiem ] / Carbohyd. Res. DOI
18	Enzyme-mediated regioselective acylations of sophorolipids / [ Bisht,K.S.;R.A.Gross;D.L.Kaplan ] / J. Org. Chem. DOI ScienceOn
19	Enzymes for chemical synthesis / [ Koeller,K.M.;C.H.Wong ] / Nature DOI ScienceOn
20	Towards the selective acylation of secondary hydroxyl groups of enzyme-catalyzed process / [ Pulido,R.;V.Gotor ] / Carbohyd. Res.
21	Enzymatic synthesis of a sucrose-containing linear polyester in nearly anhydrous organic media / [ Patil,D.R.;D.G.Rethwisch;J.S.Dordick ] / Biotechnol. Bioeng. DOI
22	Eine Methode der Enzymatischen Estersynthesen / [ Sym,E.A. ] / Enzymologia
23	Method for producing cacao butter substitute / [ Matsuo,T;N.Sawamura;Y.Hashimoto;W.Hashida ] / US Patent 4,268,527
24	Kinetic resolution of chiral amines ω-transaminase using an enzymemembrane reactor / [ Shin,J.S.;B.G.Kim ] / Biotechnol. Bioeng. DOI ScienceOn
25	Enzymatic catalysis in organic media at 100°C / [ Zaks,A.;A.M.Klibanov ] / Science DOI ScienceOn
26	Controlling enzyme-catalyzed regioselectivity in sugar ester synthesis / [ Rich,J.O.;B.A.Bedell;J.S.Dordick ] / Biotechnol. Bioeng. DOI ScienceOn
27	Counting on chiral drugs / [ Stinson,S.C. ] / Chem. Eng. News
28	Chemoenzymatic synthesis of a sucrose-containing aromatic polymers / [ Park,H.G.;H.N.Chang;J.S.Dordick ] / Biotechnol. Bioeng. DOI ScienceOn
29	Chemical and biochemical catalysis to make swellable polymers / [ Dordick,J.S.;R.J.Linhardt;D.G.Rethwisch ] / Chemtech.
30	Concerining lipase, the fat-splitting enzyme, and the reversibility of its action / [ Kastle,J.H.;A.S.Lovenhart ] / Am. Chem. J.
31	Enzyme catalyzed processes in organic solvents / [ Zaks,A.;A.M.Klibanov ] / Proc. Natl. Acad. Sci. USA DOI ScienceOn
32	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 ] / J. Mol. Catal. B-Enzym. DOI ScienceOn
33	Biotransformations in the discovery and development of pharmaceuticals / [ Zaks,A.;D.R.Dodds ] / Curr. Opin. Drug. Discov. Dev.
34	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 ] / J. Org. Chem. DOI
35	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 ] / Biotechnol. Bioeng. DOI ScienceOn
36	Protease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide / [ Riva,S.;J.Chopineau;A.P.G.Kieboom;A.M.Klibanov ] / J. Am. Chem. Soc. DOI
37	Regioselective acylation of secondary hydroxyl groups in sugars catalyzed by lipases in organic solvents / [ Therisod,M.;A.M.Klibanov ] / J. Am. Chem. Soc. DOI
38	/ [ Wong,C.H.;G.M.Whitesides ] / Enzymes in Synthetic Organic Chemistry
39	Enzymes in organic synthesis / [ Jones,J.B. ] / Tetrahedron DOI ScienceOn
40	Enzymatic resolution of racemic ibuprofen by lipase-catalyzed esterification reaction:Effects of water content and solid supports / [ Kim,M.G.;S.B.Lee ] / J. Ferment. Bioeng. DOI ScienceOn

1	/ Organic and Biomolecular Chemistry
2	/ Biochemical Engineering Journal
3	/ Chinese Journal of Chemistry
4	/ Applied Biochemistry and Biotechnology - Part A Enzyme Engineering and Biotechnology
5	/ Biotechnology and Bioprocess Engineering
6	/ Tetrahedron Asymmetry
7	/ Tetrahedron
8	/ Magnetic Resonance in Chemistry
9	/ Bioorganic and Medicinal Chemistry Letters
10	/ Applied Microbiology and Biotechnology
11	/ Food Chemistry
12	/ Biotechnology and Bioprocess Engineering