Acta NaturaeActa NaturaeActa Naturae2075-8251Acta Naturae Ltd1077410.32607/20758251-2010-2-1-94-96ArticlesСтатьиResearch ArticlePenicillin Acylase-Catalyzed Effective and Stereoselective Acylation of 1-phenylethylamine in Aqueous Medium using Non-Activated Acyl DonorPenicillin Acylase-Catalyzed Effective and Stereoselective Acylation of 1-phenylethylamine in Aqueous Medium using Non-Activated Acyl DonorGurandaD T

Faculty of Bioengineering and Bioinformatics

UshakovG A

Faculty of Bioengineering and Bioinformatics

SvedasV Kvytas@belozersky.msu.ruBelozersky Institute of Physicochemical BiologyLomonosov Moscow State University1503201021VOL 2, NO1 (2010)ТОМ 2, №1 (2010)949617012020Copyright ©; 2010, Guranda D.T., Ushakov G.A., Svedas V.K.Copyright ©; 2010, Guranda D.T., Ushakov G.A., Svedas V.K.2010Guranda D.T., Ushakov G.A., Svedas V.K.Guranda D.T., Ushakov G.A., Svedas V.K.https://creativecommons.org/licenses/by/4.0https://actanaturae.ru/2075-8251/article/view/10774

Until recently the biocatalytic preparation of enantiomerically pure amines was based on stereoselective acyl transfer in an organic medium using activated acyl donors. The possibility of performing an effective and enantioselective enzymatic acylation of amines in an aqueous medium without using activated acyl donors was demonstrated for the first time as the example of direct condensation of phenylacetic acid and racemic 1-phenylethylamine. Direct condensation of the acid and the amine took place at mild reaction conditions with a high initial rate (3.3 μmole/(l∙h)), degree of conversion (80% acylation of active amine enantiomer), and enantioselectivity (enantiomeric excess of the product was more than 95%). The suggested approach has remarkable advantages compared to enzymatic reactions in organic media and is of practical value for the biocatalytic preparation of enantiomerically pure compounds at mild conditions using readily available reagents.

stereoselective enzymatic acylation in aqueous mediumdirect condensationenantiomerically pure compoundspenicillin acylaseMoorcroft M. Biocatalysis shines for chiral manufacture. Frost & Sullivan Market Insight. 2003; http://chemicals.frost.com/prod/servlet/market-insight-top.pag?docid= 4056760&ctxixpLink=FcmCtx7&ctxixpLabel=FcmCtx8Understanding chiral technologies. Pharma-reports. 2008; http://www.reportbuyer.com/pharma_healthcare/research_r_d/understanding_chiral_technologies.htmlVan Rantwijk F., Sheldon R.A. // Tetrahedron. 2004. V. 60. P. 501-519.Methods in Biotechnology. Walker J.M., Series Editor. 15. Enzymes in Nonaqueous Solvents: Methods and Protocols, edited by Vulfson E.N., Halling P.J. and Holland H.L., Humana Press Inc., 2001. 679 p.Bornscheuer U.T., Kazlauskas R.J., Hydrolases in Organic Synthesis. Wiley-VCH Verlag GmbH, 2006.Klibanov A.M. // Nature. 2001. V. 409. P. 241-246.Lee M.-Y., Dordick J.S. // Current Opinion Biotechnol. 2002. 13. P. 376-384.Carrea G., Riva S. // Angew. Chem. Int. Ed. Engl. 2000. 39(13). P. 2226-2254.Schmid A., Dordick J.S., Hauer B., Kiener A., Wubbolts M., Witholt B. // Nature. 2001. V. 409. P. 258-268.Jaeger K.-E., Liebeton K., Zonta A., Schimossek K., Reetz M.T. // Appl. Microb. Technol. 1996. V. 46. P. 99-105.Takayama S., Lee S.T.; Hung, S.C., Wong C.H. // Chem. Commun. 1999. P. 127-128.Iglesias L.E., Rebolledo F., Gotor V. // Tetrahedron: Asymmetry. 2000. V. 11. P. 1047-1050.Klibanov A.M. // Trends Biotechnol. 1997. V. 15. P. 97-101.Carey J.S., Laffan D., Thomson C., Williams M.T. // Org. Biomol. Chem. 2006. V. 4. P. 2337-2347.Guranda D.T., Van Langen L.M., Van Rantwijk F., Sheldon R.A., Svedas V.K. // Tetrahedron: Asymmetry. 2001. V. 12. P. 1645-1650.Svedas V., Guranda D., Van Langen L., Van Rantwijk F., Sheldon R. // FEBS Lett. 1997. V. 417. № 3. P. 414-418.Juaristi E., Escalante J., Leon-Romo J.L. and Reyes A. // Tetrahedron: Asymmetry. 1998. V. 9. P. 715-740.Juaristi E., Leon-Romo J.L., Reyes A. and Escalante J. // Tetrahedron: Asymmetry. 1999. V. 10. P. 2441-2495.Svedas V.K., Savchenko M.V., Beltser A.I., Guranda D.F. // Ann. N.-Y. Acad. Sci. 1996. V. 799. P. 659-669.Galunsky B., Lummer K., Kasche V. // Monatsh. Chem. 2000. V. 131. P. 623-632.Guranda D.T., Khimiuk A.I., Van Langen L.M., Van Rantwijk F., Sheldon R.A., Svedas V.K. // Tetrahedron: Asymmetry. 2004. V. 15. P. 2901-2906.