3.3. 4 Biocatalytic Oxidation of Alcohols: An Overview
Book
Editors: Clarke, P. A.; Joule, J. A.; Marsden, S. P.; Petersson, E. J.
Title: Knowledge Updates 2021/3
Print ISBN: 9783132442092; Online ISBN: 9783132442115; Book DOI: 10.1055/b000000500
1st edition © 2021 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Knowledge Updates
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.
Type: Multivolume Edition
Abstract
This chapter provides a representative, but non-exhaustive, overview of biocatalytic methods for the oxidation of alcohols to the corresponding carbonyl products. Enzymes represent an attractive alternative to established oxidation catalysts, especially if mild reaction conditions are needed or if regio- or stereoselectivity are desirable.
Key words
alcohol dehydrogenases - alcohol oxidases - alcohol oxidation - aldehyde synthesis - biocatalysis - carboxylate synthesis - ketone synthesis - oxidative kinetic resolution - regioselective oxidation - stereoselective oxidation-
3 Palfey BA, Massey V, In: Radical Reactions and Oxidation/Reduction Sinnott M. Academic San Diego 1998; 83
-
10 Lavandera I, Kern A, Resch V, Ferreira-Silva B, Glieder A, Fabian WMF, de Wildeman S, Kroutil W. Org. Lett. 2008; 10: 2155
-
13 Dias Gomes M, Bommarius BR, Anderson SR, Feske BD, Woodley JM, Bommarius AS. Adv. Synth. Catal. 2019; 361: 2574
-
24 Könst P, Kara S, Kochius S, Holtmann D, Arends IWCE, Ludwig R, Hollmann F. ChemCatChem 2013; 5: 3027
-
25 Kochius S, Park JB, Ley C, Könst P, Hollmann F, Schrader J, Holtmann D. J. Mol. Catal. B: Enzym. 2014; 103: 94
-
27 Haas J, Schätzle MA, Husain SM, Schulz-Fincke J, Jung M, Hummel W, Müller M, Lüdeke S. Chem. Commun. (Cambridge) 2016; 52: 5198
-
30 Kochius S, Ni Y, Kara S, Gargiulo S, Schrader J, Holtmann D, Hollmann F. ChemPlusChem 2014; 79: 1554
-
34 Van Hecke W, Salaheddin C, Ludwig R, Dewulf J, Haltrich D, Van Langenhove H. Bioresour. Technol. 2009; 100: 5566
-
35 Van Hecke W, Ludwig R, Dewulf J, Auly M, Messiaen T, Haltrich D, Van Langenhove H. Biotechnol. Bioeng. 2009; 102: 122
-
36 Ludwig R, Ozga M, Zámocky M, Peterbauer C, Kulbe KD, Haltrich D. Biocatal. Biotransform. 2004; 22: 97
-
37 Baminger U, Ludwig R, Galhaup C, Leitner C, Kulbe KD, Haltrich D. J. Mol. Catal. B: Enzym. 2001; 11: 541
-
44 Heath RS, Birmingham WR, Thompson MP, Taglieber A, Daviet L, Turner NJ. ChemBioChem 2019; 20: 276
-
46 Mathieu Y, Offen WA, Forget SM, Ciano L, Viborg AH, Blagova E, Henrissat B, Walton PH, Davies GJ, Brumer H. ACS Catal. 2020; 10: 3042
-
48 Nguyen Q.-T, de Gonzalo G, Binda C, Rioz-Martínez A, Mattevi A, Fraaije MW. ChemBioChem 2016; 17: 1359
-
52 Nguyen Q.-T, Romero E, Dijkman WP, de Vasconcellos SP, Binda C, Mattevi A, Fraaije MW. Biochemistry 2018; 57: 6209
-
58 Viña-Gonzalez J, Jimenez-Lalana D, Sancho F, Serrano A, Martinez AT, Guallar V, Alcalde M. Adv. Synth. Catal. 2019; 361: 2514
-
60 Viña-Gonzalez J, Gonzalez-Perez D, Ferreira P, Martinez AT, Alcalde M. Appl. Environ. Microbiol. 2015; 81: 6451
-
62 de Almeida TP, van Schie MMCH, Ma A, Tieves F, Younes SHH, Fernández-Fueyo E, Arends IWCE, Riul Jr A, Hollmann F. Adv. Synth. Catal. 2019; 361: 2668
-
63 van Schie MMCH, Pedroso de Almeida T, Laudadio G, Tieves F, Fernández-Fueyo E, Noël T, Arends IWCE, Hollmann F. Beilstein J. Org. Chem. 2018; 14: 697
-
66 Fuchs M, Schober M, Pfeffer J, Kroutil W, Birner-Gruenberger R, Faber K. Adv. Synth. Catal. 2011; 353: 2354
-
67 Hafenstine GR, Ma K, Harris AW, Yehezkeli O, Park E, Domaille DW, Cha JN, Goodwin AP. ACS Catal. 2017; 7: 568
-
68 Bechi B, Herter S, McKenna S, Riley C, Leimkühler S, Turner NJ, Carnell AJ. Green Chem. 2014; 16: 4524
-
74 Gandolfi R, Borrometi A, Romano A, Sinisterra Gago JV, Molinari F. Tetrahedron: Asymmetry 2002; 13: 2345
-
76 Habe H, Shimada Y, Yakushi T, Hattori H, Ano Y, Fukuoka T, Kitamoto D, Itagaki M, Watanabe K, Yanagishita H, Matsushita K, Sakaki K. Appl. Environ. Microbiol. 2009; 75: 7760
-
77 Geerlof A, Jongejan JA, van Dooren TJGM, Raemakers-Franken PC, van den Tweel WJJ, Duine JA. Enzyme Microb. Technol. 1994; 16: 1059
-
78 Geerlof A, Stoorvogel J, Jongejan JA, Leenen EJTM, van Dooren TJGM, van den Tweel WJJ, Duine JA. Appl. Microbiol. Biotechnol. 1994; 42: 8
-
81 Gandolfi R, Cavenago K, Gualandris R, Sinisterra Gago JV, Molinari F. Process Biochem. (Oxford, U. K.) 2004; 39: 749
-
82 De Vitis V, Dall’Oglio F, Tentori F, Contente ML, Romano D, Brenna E, Tamborini L, Molinari F. Catalysts 2019; 9: 208
-
83 Brenna E, Cannavale F, Crotti M, De Vitis V, Gatti FG, Migliazza G, Molinari F, Parmeggiani F, Romano D, Santangelo S. ChemCatChem 2016; 8: 3796
-
88 Boratyński F, Pannek J, Walczak P, Janik-Polanowicz A, Huszcza E, Szczepańska E, Martinez-Rojas E, Olejniczak T. Process Biochem. (Oxford, U. K.) 2014; 49: 1637
-
98 Kara S, Spickermann D, Schrittwieser JH, Weckbecker A, Leggewie C, Arends IWCE, Hollmann F. ACS Catal. 2013; 3: 2436
-
100 Scherkus C, Schmidt S, Bornscheuer UT, Gröger H, Kara S, Liese A. Biotechnol. Bioeng. 2017; 114: 1215
-
101 Oberleitner N, Ressmann AK, Bica K, Gärtner P, Fraaije MW, Bornscheuer UT, Rudroff F, Mihovilovic MD. Green Chem. 2017; 19: 367
-
103 Schmidt S, Scherkus C, Muschiol J, Menyes U, Winkler T, Hummel W, Gröger H, Liese A, Herz H.-G, Bornscheuer UT. Angew. Chem. Int. Ed. 2015; 54: 2784
-
107 Srinivasamurthy VST, Böttcher D, Engel J, Kara S, Bornscheuer UT. Process Biochem. (Oxford, U. K.) 2020; 88: 22
-
109 Huang L, Romero E, Ressmann AK, Rudroff F, Hollmann F, Fraaije MW, Kara S. Adv. Synth. Catal. 2017; 359: 2142
-
110 Tan T.-C, Kracher D, Gandini R, Sygmund C, Kittl R, Haltrich D, Hällberg BM, Ludwig R, Divne C. Nat. Commun. 2015; 6: 7542
-
118 Gandomkar S, Jost E, Loidolt D, Swoboda A, Pickl M, Elaily W, Daniel B, Fraaije MW, Macheroux P, Kroutil W. Adv. Synth. Catal. 2019; 361: 5264
-
120 Ramírez MA, Pérez HI, Manjarrez N, Solís A, Luna H, Cassani J. Electron. J. Biotechnol. 2008; 11
-
123 Kochius S, Paetzold M, Scholz A, Merkens H, Vogel A, Ansorge-Schumacher M, Hollmann F, Schrader J, Holtmann D. J. Mol. Catal. B: Enzym. 2014; 103: 61
-
125 Voss CV, Gruber CC, Faber K, Knaus T, Macheroux P, Kroutil W. J. Am. Chem. Soc. 2008; 130: 13 969
-
126 Xue Y.-P, Zheng Y.-G, Zhang Y.-Q, Sun J.-L, Liu Z.-Q, Shen Y.-C. Chem. Commun. (Cambridge) 2013; 49: 10 706
-
128 Fragnelli MC, Hoyos P, Romano D, Gandolfi R, Alcántara AR, Molinari F. Tetrahedron 2012; 68: 523
-
131 Mutti FG, Knaus T, Scrutton NS, Breuer M, Turner NJ. Science (Washington, D. C.) 2015; 349: 1525