Biocatalytic synthesis of optically active tertiary alcohols

Applied Microbiology and Biotechnology

Volumn 91, Issue 3, 2011, Pages 505-517

  Kourist, Robert ^a   Bornscheuer, Uwe T ^b  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

Enantioselectivity; Enzyme catalysis; Esterase; Protein engineering; Tertiary alcohols

Indexed keywords

BIOCATALYSIS; BIOCATALYTIC SYNTHESIS; BUILDING BLOCKES; CHEMICAL SYNTHESIS; CHEMOENZYMATIC ROUTE; CYCLASES; ENZYMATIC PREPARATION; ENZYME CATALYSIS; EPOXIDE HYDROLASES; ESTERASE; HALOHYDRINS; HEAVY METAL CATALYSTS; OPTICALLY ACTIVE; PROTEIN ENGINEERING; TERTIARY ALCOHOLS;

CATALYSTS; ENANTIOSELECTIVITY; ESTERS; GENETIC ENGINEERING; HEAVY METALS; LIPASES; OLEFINS; SYNTHESIS (CHEMICAL);

BIOCHEMICAL ENGINEERING;

ACYLTRANSFERASE; ALCOHOL; EPOXIDE HYDROLASE; ESTERASE; HALOHYDRIN DEHALOGENASE DERIVATIVE; HYDROLASE; HYDROLYASE; LYASE; TERPENE CYCLASE DERIVATIVE; TERTIARY ALCOHOL; THIAMINE DIPHOSPHATE DEPENDENT ENZYME DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ALCOHOL; CATALYSIS; ENZYME ACTIVITY; PROTEIN; SUSTAINABILITY;

BIOCATALYSIS; NONHUMAN; REVIEW;

ALCOHOLS; BACTERIA; BIOCATALYSIS; HYDROLASES; PROTEIN ENGINEERING; TERPENES;

EID: 79960723164     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-011-3418-9     Document Type: Review

References (63)

1. SA Agger F Lopez-Gallego TR Hoye C Schmidt-Dannert 2008 Identification of sesquiterpene synthases from Nostoc punctiforme PCC 73102 and Nostoc sp. strain PCC 7120 J Bacteriol 190 6084 6096 10.1128/JB.00759-08 1:CAS:528: DC%2BD1cXhtFSrsrfP
2. PK Ajikumar WH Xiao KEJ Tyo Y Wang F Simeon E Leonard O Mucha TH Phon B Pfeifer G Stephanopoulos 2010 Isoprenoid pathway optimization for taxol precursor overproduction in Escherichia coli Science 330 70 74 10.1126/science.1191652 1:CAS:528:DC%2BC3cXht1WmtbnO
3. JN Andexer JV Langermann U Kragl M Pohl 2009 How to overcome limitations in biotechnological processes-examples from hydroxynitrile lyase applications Trends Biotechnol 27 599 607 10.1016/j.tibtech.2009.07.005 1:CAS:528: DC%2BD1MXhtFajsrfP
4. M Avi MH Fechter K Gruber F Bela P Pochlauer H Griengl 2004 Hydroxynitrile lyase catalysed synthesis of heterocyclic (R)- and (S)-cyanohydrins Tetrahedron 60 10411 10418 10.1016/j.tet.2004.07.099 1:CAS:528:DC%2BD2cXotlWgurY%3D (Pubitemid 39330624)
5. S Bartsch R Kourist UT Bornscheuer 2008 Complete inversion of enantioselectivity towards acetylated tertiary alcohols by a double mutant of a Bacillus subtilis esterase Angew Chem Int Ed 47 1508 1511 10.1002/anie.200704606
6. A Bassegoda GS Nguyen M Schmidt R Kourist P Diaz UT Bornscheuer 2010 Rational protein design of Paenibacillus barcinonensis esterase EstA for kinetic resolution of tertiary alcohols ChemCatChem 2 962 967 10.1002/cctc.201000053 1:CAS:528:DC%2BC3cXpslCgu74%3D
7. J Bohlmann G Meyer-Gauen R Croteau 1998 Plant terpenoid synthases: molecular biology and phylogenetic analysis Proc Natl Acad Sci U S A 95 4126 4133 10.1073/pnas.95.8.4126 1:CAS:528:DyaK1cXis1Ohtrs%3D (Pubitemid 28207876)
8. Bosley JA, Casey J, Macrae AR, MyCock G (1994) Process for the esterification of carboxylic acids with tertiary alcohols. WO 95/01450
9. Brodkorb D, Harder J (2009) First enzymatic insight in anaerobic monoterpenes degradation. Characterization of the first initial steps. Biotrans 2009. Conference proceedings
10. D Brodkorb M Gottschall R Marmulla F Luddeke J Harder 2010 Linalool dehydratase-isomerase, a bifunctional enzyme in the anaerobic degradation of monoterpenes J Biol Chem 285 30436 30442 10.1074/jbc.M109.084244 1:CAS:528:DC%2BC3cXht1SlsrzF
11. DE Cane RM Watt 2003 Expression and mechanistic analysis of a germacradienol synthase from Streptomyces coelicolor implicated in geosmin biosynthesis Proc Natl Acad Sci U S A 100 1547 1551 10.1073/pnas.0337625100 1:CAS:528:DC%2BD3sXhsFGktrc%3D (Pubitemid 36254484)
12. WJ Choi 2009 Biotechnological production of enantiopure epoxides by enzymatic kinetic resolution Appl Microbiol Biotechnol 84 239 247 10.1007/s00253-009-2110-9 1:CAS:528:DC%2BD1MXpsVarsLs%3D
13. Christoffers J, Baro A (2005) Quaternary stereocenters, challenges and solutions for organic synthesis. Wiley-VCH, Weinheim
14. Chipman D, Barak Z, Schloss JV (1998) Biosynthesis of 2-aceto-2-hydroxy acids: acetolactate synthases and acetohydroxyacid synthases. Biochim Biophys Act 1385:401-419 (Pubitemid 28310803)
15. PG Cozzi R Hilgraf N Zimmermann 2007 Enantioselective catalytic formation of quaternary stereogenic centers Eur J Org Chem 2007 36 5969 5994 10.1002/ejoc.200700318
16. AL Crowell DC Williams EM Davis MR Wildung R Croteau 2002 Molecular cloning and characterization of a new linalool synthase Arch Biochem Biophys 405 112 121 10.1016/S0003-9861(02)00348-X 1:CAS:528:DC%2BD38XmtFShsbY%3D (Pubitemid 35033497)
17. J Degenhardt TG Kollner J Gershenzon 2009 Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants Phytochemistry 70 1621 1637 10.1016/j.phytochem.2009.07.030 1:CAS:528:DC%2BD1MXhsVWls7bL
18. P Dominguez de Maria C Carboni-Oerlemans B Tuin G Bargeman A van der Meer R van Gemert 2005 Biotechnological applications of Candida antarctica lipase A: state-of-the-art J Mol Catal B Enzym 37 36 46 10.1016/j.molcatb.2005.09.001 1:CAS:528:DC%2BD2MXht1Gnur3E (Pubitemid 41674646)
19. Enders D, Balensiefer T, Niemeier O, Christmann M (2007) Enantioselective organocatalysis. Wiley-VCH, Weinheim
20. DJ Ericsson A Kasrayan P Johanssonl T Bergfors AG Sandström JE Bäckvall SL Mowbray 2008 X-ray structure of Candida antarctica lipase A shows a novel lid structure and a likely mode of interfacial activation J Mol Biol 376 109 119 10.1016/j.jmb.2007.10.079 1:CAS:528:DC%2BD1cXpt1ynsA%3D%3D
21. MH Fechter K Gruber M Avi W Skranc C Schuster P Pochlauer KO Klepp H Griengl 2007 Stereoselective biocatalytic synthesis of (S)-2-hydroxy-2- methylbutyric acid via substrate engineering by using "thio-disguised" precursors and oxynitrilase catalysis Chem Eur J 13 3369 3376 10.1002/chem.200601114 1:CAS:528:DC%2BD2sXksleiu74%3D (Pubitemid 46925644)
22. M Gall R Kourist M Schmidt UT Bornscheuer 2010 The role of the GGGX motif in determining the activity and enantioselectivity of pig liver esterase towards tertiary alcohols Biocatal Biotransform 28 201 208 10.3109/ 10242421003753803 1:CAS:528:DC%2BC3cXotlSkt7k%3D
23. Y Hasegawa ID Gridnev T Ikariya 2010 Enantioselective and Z/E-selective conjugate addition of alpha-substituted cyanoacetates to acetylenic esters catalyzed by bifunctional ruthenium and iridium complexes Angew Chem Int Ed 49 8157 8160 10.1002/anie.201003585 1:CAS:528:DC%2BC3cXhtlalu7%2FO
24. B Heinze R Kourist L Fransson K Hult UT Bornscheuer 2007 Highly enantioselective kinetic resolution of a tertiary alcohol using mutants of an esterase from Bacillus subtilis Prot Eng Des Sel 20 125 131 10.1093/protein/ gzm003 1:CAS:528:DC%2BD2sXlt1Ortb8%3D (Pubitemid 46536746)
25. H Hellström A Steinreiber SF Mayer K Faber 2001 Bacterial epoxide hydrolase-catalyzed resolution of a 2,2-disubstituted oxirane: optimization and upscaling Biotechnol Lett 23 169 173 10.1023/A:1005636121060 (Pubitemid 32147411)
26. E Henke J Pleiss UT Bornscheuer 2002 Activity of lipases and esterases towards tertiary alcohols: insights into structure-function relationships Angew Chem Int Ed 41 3211 3213 10.1002/1521-3773(20020902)41:17<3211::AID- ANIE3211>3.0.CO;2-U 1:CAS:528:DC%2BD38XntFWku7s%3D (Pubitemid 35014389)
27. E Henke UT Bornscheuer RD Schmid J Pleiss 2003 A molecular mechanism of enantiorecognition of tertiary alcohols by carboxylesterases Chembiochem 4 485 493 10.1002/cbic.200200518 1:CAS:528:DC%2BD3sXkslCitbc%3D (Pubitemid 36749618)
28. S Herter GS Nguyen ML Thompson F Steffen-Munsberg F Schauer UT Bornscheuer R Kourist 2011 Comparative analysis of tertiary alcohol esterase activity in bacterial strains isolated from enrichment cultures and from screening strain libraries Appl Microbiol Biotechnol 90 929 939 10.1007/s00253-011-3124-7 1:CAS:528:DC%2BC3MXks1Wntr4%3D
29. Hiseni A, Arends IW, Otten LG (2011) Biochemical characterization of the carotenoid 1,2-hydratases (CrtC) from Rubrivivax gelatinosus and Thiocapsa roseopersicina. Appl Microbiol Biotechnol. doi: 10.1007/s00253-011-3324-1
30. J Holt U Hanefeld 2009 Enantioselective enzyme-catalysed synthesis of cynohydrins Curr Org Synth 6 15 37 10.2174/157017909787314858 1:CAS:528:DC%2BD1MXkslCnu78%3D
31. J Holt IWCE Arends A Minnaard U Hanefeld 2007 Hydrolase-catalysed preparation of chiral alpha, alpha-disubstituted cyanohydrin acetates Adv Synth Catal 349 1341 1344 10.1002/adsc.200700053 1:CAS:528:DC%2BD2sXntVSjtb0%3D
32. Y Hotta S Ezaki H Atomi T Imanaka 2002 Extremely stable and versatile carboxylesterase from a hyperthermophilic archaeon Appl Environ Microbiol 68 3925 3931 10.1128/AEM.68.8.3925-3931.2002 1:CAS:528:DC%2BD38XmtVejsr8%3D (Pubitemid 34836705)
33. Hou CT, Adachi S (2005) Handbook of industrial biocatalysis. CRC Taylor & Francis, Boca Raton
34. M Komatsu M Tsuda S Omura H Oikawa H Ikeda 2008 Identification and functional analysis of genes controlling biosynthesis of 2-methylisoborneol Proc Natl Acad Sci U S A 105 7422 7427 10.1073/pnas.0802312105 1:CAS:528: DC%2BD1cXmvFOltL0%3D (Pubitemid 351830033)
35. R Kourist S Bartsch UT Bornscheuer 2007 Highly enantioselective synthesis of arylaliphatic tertiary alcohols using mutants of an esterase from Bacillus subtilis Adv Synth Catal 349 1393 1398 10.1002/adsc.200600641 1:CAS:528:DC%2BD2sXntVSjur8%3D
36. R Kourist SH Krishna JS Patel F Bartnek TS Hitchman DP Weiner UT Bornscheuer 2007 Identification of a metagenome-derived esterase with high enantioselectivity in the kinetic resolution of arylaliphatic tertiary alcohols Org Biomol Chem 5 3310 3313 10.1039/b709965g 1:CAS:528:DC%2BD2sXhtFSnt7bL (Pubitemid 47519068)
37. R Kourist P Dominguez de Maria UT Bornscheuer 2008 Enzymatic synthesis of optically active tertiary alcohols: expanding the biocatalysis toolbox Chembiochem 9 491 498 10.1002/cbic.200700688 1:CAS:528:DC%2BD1cXlt1Wht70%3D
38. R Kourist GS Nguyen D Strübing D Böttcher K Liebeton C Naumer J Eck UT Bornscheuer 2008 Hydrolase-catalyzed stereoselective preparation of protected alpha, alpha-dialkyl-alpha-hydroxycarboxylic acids Tetrahedron Asymmetry 19 1839 1843 10.1016/j.tetasy.2008.07.005 1:CAS:528:DC%2BD1cXhtVWksrbO
39. R Kourist H Jochens S Bartsch R Kuipers S Kumar Padhi M Gall D Böttcher H-J Joosten UT Bornscheuer 2010 The alpha/beta-hydrolase fold 3DM database (ABHDB) as a tool for protein engineering Chembiochem 11 1635 1643 10.1002/cbic.201000213 1:CAS:528:DC%2BC3cXpvV2jsr4%3D
40. R Kourist H Brundiek UT Bornscheuer 2010 Protein engineering and discovery of lipases Eur J Lipid Sci Technol 112 64 74 10.1002/ejlt.200900143 1:CAS:528:DC%2BC3cXht12nurY%3D
41. SH Krishna M Persson UT Bornscheuer 2002 Enantioselective transesterification of a tertiary alcohol by lipase A from Candida antarctica Tetrahedron Asymmetry 13 2693 2696 10.1016/S0957-4166(02)00739-5 (Pubitemid 35454025)
42. C Landmann B Fink M Festner M Dregus KH Engel W Schwab 2007 Cloning and functional characterization of three terpene synthases from lavender (Lavandula angustifolia) Arch Biochem Biophys 465 417 429 10.1016/j.abb.2007.06.011 1:CAS:528:DC%2BD2sXhtVWmtrfO (Pubitemid 47361999)
43. O Larkov A Zaks E Bar E Lewinsohn N Dudai AM Mayer U Ravid 2008 Enantioselective monoterpene alcohol acetylation in Origanum, Mentha and Salvia species Phytochemistry 69 2565 2571 10.1016/j.phytochem.2008.07.018 1:CAS:528:DC%2BD1cXht12rtrfM
44. P Lehwald M Richter C Rohr HW Liu M Müller 2010 Enantioselective intermolecular aldehyde-ketone cross-coupling through an enzymatic carboligation reaction Ang Chem Int Ed 49 2389 2392 1:CAS:528:DC%2BC3cXjslGlu70%3D
45. Lutz S, Bornscheuer UT (eds) (2008) Protein engineering handbook. Wiley-VCH, Weinheim
46. M Majeric-Elenkov HW Hoeffken L Tang B Hauer DB Janssen 2007 Enzyme-catalyzed nucleophilic ring opening of epoxides for the preparation of enantiopure tertiary alcohols Adv Synth Catal 349 2279 2285 10.1002/adsc. 200700146
47. M Majeric-Elenkov LX Tang A Meetsma B Hauer DB Janssen 2008 Formation of enantiopure 5-substituted oxazolidinones through enzyme-catalysed kinetic resolution of epoxides Org Lett 10 2417 2420 10.1021/ol800698t
48. MD Mihovilovic HG Leisch K Mereiter 2004 Microwave-mediated intramolecular Diels-Alder cyclization of biodihydroxylated benzoic acid derivatives Tetrahedron Lett 45 7087 7090 10.1016/j.tetlet.2004.07.109 1:CAS:528:DC%2BD2cXntVKqt7g%3D (Pubitemid 39178570)
49. C Molinaro AA Guilbault B Kosjek 2010 Resolution of 2,2-disubstituted epoxides via biocatalytic azidolysis Org Lett 12 3772 3775 10.1021/ol101406k 1:CAS:528:DC%2BC3cXps1Whuro%3D
50. GS Nguyen R Kourist M Paravidino A Hummel J Rehdorf RVA Orru U Hanefeld UT Bornscheuer 2010 An enzymatic toolbox for the kinetic resolution of 2-(pyridinyl)but-3-yn-2-ols and tertiary cyanohydrins Eur J Org Chem 14 2753 2758
51. D O'Hagan NA Zaidi 1992 Hydrolytic resolution of tertiary acetylenic acetate esters with the lipase from Candida cylindracea J Chem Soc Perkin Trans 1 947 949 10.1039/p19920000947
52. D Özdemirhan S Sezer Y Sonmez 2008 Enzyme-catalyzed resolution of aromatic ring fused cyclic tertiary alcohols Tetrahedron Asymmetry 19 2717 2720 10.1016/j.tetasy.2008.12.002
53. M Paravidino J Holt D Romano N Singh I Arends AJ Minnaard RVA Orru F Molinari U Hanefeld 2010 Microbial-catalysed resolution of sterically demanding cyanohydrins J Mol Catal B Enzym 63 87 92 10.1016/j.molcatb.2009.12.014 1:CAS:528:DC%2BC3cXht12qu7w%3D
54. J Pleiss M Fischer M Peiker C Thiele RD Schmid 2000 Lipase engineering database-understanding and exploiting sequence-structure-function relationships J Mol Catal B Enzym 10 491 508 10.1016/S1381-1177(00)00092-8 1:CAS:528:DC%2BD3cXls1Gitbs%3D (Pubitemid 30628635)
55. M Pogorevc K Faber 2000 Biocatalytic resolution of sterically hindered alcohols, carboxylic acids and esters containing fully substituted chiral centers by hydrolytic enzymes J Mol Catal B Enzym 10 357 376 10.1016/S1381-1177(99)00121-6 1:CAS:528:DC%2BD3cXltlWgsbc%3D (Pubitemid 30483990)
56. T Purkarthofer W Skranc C Schuster H Griengl 2007 Potential and capabilities of hydroxynitrile lyases as biocatalysts in the chemical industry Appl Microbiol Biotechnol 76 309 320 10.1007/s00253-007-1025-6 1:CAS:528:DC%2BD2sXotVOgtr8%3D (Pubitemid 47101689)
57. K Rashamuse V Magomani T Ronneburg D Brady 2009 A novel family VIII carboxylesterase derived from a leachate metagenome library exhibits promiscuous beta-lactamase activity on nitrocefin Appl Microbiol Biotechnol 83 491 500 10.1007/s00253-009-1895-x 1:CAS:528:DC%2BD1MXmt1Sjurk%3D
58. D Seebach 2011 Generation of secondary, tertiary, and quaternary centers by geminal disubstitution of carbonyl oxygens Angew Chem Int Ed 50 96 101 10.1002/anie.201003823 1:CAS:528:DC%2BC3cXhs1alu7rI
59. RP Sonawane V Jheengut C Rabalakos R Larouche-Gauthier HK Scott VK Aggarwal 2011 Enantioselective construction of quaternary stereogenic centers from tertiary boronic esters: methodology and applications Angew Chem Int Ed 50 3760 3763 10.1002/anie.201008067 1:CAS:528:DC%2BC3MXkt12jt7Y%3D
60. A Steinreiber K Faber 2001 Microbial epoxide hydrolases for preparative biotransformations Curr Opin Biotechnol 12 552 558 10.1016/S0958-1669(01)00262-2 1:CAS:528:DC%2BD38Xjt1SgtQ%3D%3D (Pubitemid 34146505)
61. JL Stymiest V Bagutski RM French VK Aggarwal 2008 Enantiodivergent conversion of chiral secondary alcohols into tertiary alcohols Nature 456 778 783 10.1038/nature07592 1:CAS:528:DC%2BD1cXhsVymtrfJ
62. M Wiggers J Holt R Kourist S Bartsch I Arends AJ Minnaard UT Bornscheuer U Hanefeld 2009 Probing the enantioselectivity of Bacillus subtilis esterase BS2 for tert. alcohols J Mol Catal B Enzym 60 82 86 10.1016/j.molcatb.2009.04.003 1:CAS:528:DC%2BD1MXms1Oju7c%3D
63. Y Yoshikuni VJ Martin TE Ferrin JD Keasling 2006 Engineering cotton (+)-delta-cadinene synthase to an altered function: germacrene D-4-ol synthase Chem Biol 13 91 98 10.1016/j.chembiol.2005.10.016 1:CAS:528: DC%2BD28XmsV2qtw%3D%3D (Pubitemid 43099927)