Browse > Article
http://dx.doi.org/10.9713/kcer.2013.51.6.716

Recent Developments and Prospects in the Enzymatic Acylations  

Park, Oh-Jin (Department of Biological and Chemical Engineering, Yanbian University of Science and Technology)
Publication Information
Korean Chemical Engineering Research / v.51, no.6, 2013 , pp. 716-726 More about this Journal
Abstract
Enzymatic acylations catalyzed by hydrolytic enzymes, along with enzymatic hydrolysis, are established reactions in the synthesis of fine chemicals such as chiral intermediates and polymerizations in the industry. Those reactions have been carried out mostly in organic media due to the thermodynamic limitations. Recently, there have been reports on enzymatic acylations in aqueous media. They have dealt with the elucidation of reaction mechanisms of hydrolases and acyl transferases based on their X-ray structures, homology comparison of the two kinds of enzymes, substrate engineering of acyl donors and computational design of acyl transferases for enzymatic acylations in aqueous media. Enzymatic acylations play an important role in the combinatorial synthesis of natural products such as polyketides and nonribosomal peptides. In this review, the historic developments of enzymatic acylations and industrial examples are described briefly. In addition, recent developments of enzymatic acylations in the modification of natural products and their prospects will be discussed.
Keywords
Enzymes; Biocatalysis; Acylations; Regioselectivity; Natural Products; Combinatorial Biosynthesis;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
연도 인용수 순위
1 McCabe, R. W. and Taylor, A., "Synthesis of Novel Polyurethane Polyesters Using the Enzyme Candida antarctica Lipase B," Green Chem., 6, 151-155(2004).   DOI   ScienceOn
2 Roberts, S. M., "Preparative Biotransformations : the Employment of Enzymes and Whole-cells in Synthetic Organic Chemistry," J. Chem. Soc., Perkin Trans. 1, 157-170(1998).
3 Turner, N. J. and O'Reilly, E., "Biocatalytic Retrosynthesis," Nature Chem. Biol., 9, 285-8(2013).   DOI   ScienceOn
4 Liese, A., Seelback, K. and Wandrey, C., Industrial Biotransformations, Wiley-VCH, Weinheim, 2006.
5 Strohmeier, G. A., Pichler, H., May, O. and Gruber-Khadjawi, M., "Application of Designed Enzymes in Organic Synthesis," Chem. Rev., 111, 4141-4164(2011).   DOI   ScienceOn
6 Schmid, A., Dordick, J. S., Hauer, B., Kiener, Wubbolts, A. M. and Witholt, B., "Industrial Biocatalysis Today and Tomorrow," Nature, 409, 258-268(2001).   DOI   ScienceOn
7 Bornscheuer, U. T., Huisman, G. W., Kazlauskas, R. J., Lutz, S., Moore, J. C. and Robins, K., "Engineering the Third Wave of Biocatalysis," Nature, 485, 185-194(2012).   DOI   ScienceOn
8 Park, D. and Lee, J., "Biological Conversion of Methane to Methanol," Korean J. Chem. Eng., 30(5), 977-987(2013).   DOI   ScienceOn
9 Min, E.-J. and Lee, E.-S., "Energy Consumption of Biodiesel Production Process by Supercritical and Immobilized Lipase Method," Korean Chem. Eng. Res.(HWAHAK KONGHAK), 50(2), 257-263(2012).   과학기술학회마을   DOI   ScienceOn
10 McLachlan, M. J., Sullivan, R. P. and Zhao, H., "Directed Enzyme Evolution and High-Throughput Screening in Directed Enzyme Evolution and High-Throughput Screening," in Biocatalysis for the Pharmaceutical Industry : Discovery, Development, and Manufacturing, eds. Tao, G.-Q. Lin, and A. L., Ch. 3, 45-64 John Wiley & Sons(2009).
11 Boersma, Y. L., Droge, M. J. and Quax, W. J., "Selection Strategies for Improved Biocatalysts," FEBS J., 274, 2181-2195(2007).   DOI   ScienceOn
12 Wang, M., Si, T. and Huimin, Z., "Biocatalyst Development by Directed Evolution," Biores. Technol., 115, 117-125(2012).   DOI   ScienceOn
13 Quin, M. B. and Schmidt-Dannert, C., ""Engineering of Biocatalysts: from Evolution to Creation," ACS Catal., 11017-1021(2011).
14 Faber, K., "Biotransformations in Organic Chemistry," Springer, 1997.
15 Patel, R. N., "Synthesis of Chiral Pharmaceutical Intermediates by Biocatalysis," Coord. Chem. Rev., 252, 659-701(2008).   DOI   ScienceOn
16 Zaks, A. and Klibanov, A. M., "Enzymatic Catalysis in Organic Media at $100^{\circ}C$," Science, 224, 1249-1251(1984).   DOI   ScienceOn
17 Zaks, A. and Klibanov, A. M., "Enzyme Catalyzed Processes in Organic Solvents," Proc. Natl. Acad. Sci. USA, 82, 3192-3196 (1985).   DOI   ScienceOn
18 Riva, S., Chopineau, J., Kieboom, A. P. G. and Klibanov, A. M., "Protease-catalyzed Regioselective Esterification of Sugars and Related Compounds in Anhydrous Dimethylformamide," J. Am. Chem. Soc., 110, 584-589(1988).   DOI
19 Pirie, C. M., De Mey, M., Prather, K. L. J. and Ajikumar, P. K., "Integrating the Protein and Metabolic Engineering Toolkits for Next-generation Chemical Biosynthesis," ACS Chem. Biol., 8(4), 662-672(2013).   DOI   ScienceOn
20 Kopp, F., Grunewald, J., Mahlert, C. and Marahiel, M. A., "Chemoenzymatic Design of Acidic Lipopeptide Hybrids: New Insights Into the Structure-activity Relationship of Daptomycin and A54145," Biochem., 45, 10474-10481(2006).   DOI   ScienceOn
21 Miao, V., Coeffet-Le Gal, M. F., Nguyen, K., Brian, P., Penn, J., Whiting, A., Steele, J., Kau, D., Martin, S., Ford, R., Gibson, T., Bouchard, M., Wrigley, S. K. and Baltz, R. H., "Genetic Engineering in Streptomyces roseosporus to Produce Hybrid Lipopeptide Antibiotics," Chem. Biol., 13(3), 269-276(2006).   DOI   ScienceOn
22 Nguyen, K. T., Ritz, D., Gu, J. Q., et al. Combinatorial Biosynthesis of Novel Antibiotics Related to Daptomycin," Proc. Natl. Acad. Sci., 103, 17462-17467(2006).   DOI   ScienceOn
23 Dubois, E. A. and Cohen, A. F., "Retapamulin," Br. J. Clin. Pharmacol., 69, 2-3(2010).   DOI   ScienceOn
24 De Mattos-Shipley, K., Hayes, P., Collins, C., Kilaru, S., Hartley, A., Foster, G. D. and Bailey, A. M., "Biobased Antibiotics from Basidios: a Case Study on the Identification and Manipulation of a Gene Cluster Involved in Pleuromutilin Biosynthesis from Clitopilus passeckerianus," Proc. Of the 7th Int. Conf. Mushroom Biol. Mushroom Prod. (ICMBMP7), 224-231(2011).
25 Honda, K., Kataoka, M. and Shimizu, S., "Enzymatic Preparation of D-beta-acetylthioisobutyric Acid and Cetraxate Hydrochloride Using a Stereo- and/or Regioselective Hydrolase," Appl. Microbiol. Biotechnol., 60, 288-292(2002).   DOI
26 Honda, K., Sakamoto, K., Kita, S., Kataoka, M. and Shimizu, S., "Biocatalytic Deprotection of a Cetraxate Ester by Microbacterium sp. Strain 7-1W Cells," Biosci. Biotechnol. Biochem., 67, 192-194 (2003).   DOI   ScienceOn
27 Kopp, F. and Marahiel, M. A., "Macrocyclization Strategies in Polyketide and Nonribosomal Peptide Biosynthesis," Nat. Prod. Rep. 24, 735-749(2007).   DOI   ScienceOn
28 Wang, M., Zhou, H., Wirz, M., Tang, Y. and Boddy, C. N., "A Thioesterase from An Iterative Fungal Polyketide Synthase Shows Macrocyclization and Cross Coupling Activity and May Play a Role in Controlling Iterative Cycling Through Product Offloading," Biochem., 48(27), 6288-6290(2009).   DOI   ScienceOn
29 Pinto, A., Wang, M., Horsman, M. and Boddy, C. N., "6-Deoxyerythronolide B Synthase Thioesterase-catalyzed Macrocyclization is Highly Stereoselective," Org. Lett., 14(9), 2278-81(2012).   DOI   ScienceOn
30 Walsh, C. T., "Combinatorial Biosynthesis of Antibiotics: Challenges and Opportunities," ChemBioChem, 3, 125-134(2002).
31 Kiss, G., Celebi-Olcum, N., Moretti, R., Baker, D. and Houk, K. N., "Computational Enzyme Design," Angew. Chem. Int. Ed., 52, 2-28(2013).
32 Otten, L. et al., "Enzyme Engineering for Enantioselectivity: from Trial-and-error to Rational Design?," Trends Biotechnol., 28, 46-54(2010).   DOI   ScienceOn
33 Planson, A. G., Carbonell, P., Grigoras, I. and Faulon, J. L., "Engineering Antibiotic Production and Overcoming Bacterial Resistance," Biotechnol. J., 6, 812-825 (2011).   DOI   ScienceOn
34 Debono, M., Abbott, B. J., Molloy, R. M. et al., "Enzymatic and Chemical Modifications of Lipopeptide Antibiotic A21978C: the Synthesis and Evaluation of Daptomycin (LY146032)," J. Antibiot., 41, 1093-1105(1988).   DOI
35 Robbel, L. and Marahiel, M. A., "Daptomycin, a Bacterial Lipopeptide Synthesized by a Nonribosomal Machinery," J. Biol. Chem., 285, 27501-27508(2010).   DOI   ScienceOn
36 Strieker, M. and Marahiel, M. A., "The Structural Diversity of Acidic Lipopeptide Antibiotics," ChemBioChem, 10, 607-616(2009).   DOI   ScienceOn
37 Boeck, L. D., Fukuda, D. S., Abbott, B. J. and Debono, M., "Deacylation of A21978C, An Acidic Lipopeptide Antibiotic Complex, by Actinoplanes utahensis," J. Antibiot., 41, 1085-1092 (1988).   DOI
38 Grunewald, J., Sieber, S. A., Mahlert, C., Linne, U. and Marahiel, M. A., "Synthesis and Derivatization of Daptomycin: a Chemoenzymatic Route to Acidic Lipopeptide Antibiotics," J. Am. Chem. Soc., 126(51), 17025-17031(2004).   DOI   ScienceOn
39 Shao, L., Li, J., Liu, A., Chang, Q., Lin, H. and Chen, D., "Efficient Bioconversion of Echinocandin B to Its Nucleus by Overexpression of Deacylase Genes in Different Host Strains," Appl. Environ. Microb., 79(4), 1126-1133(2012).
40 D'Costa, V. M., Mukhtar, T. A., Patel, T., Koteva, K., Waglechner, N., Hughes, D. W., Wright, G. D. and De Pascale G., "Inactivation of the Lipopeptide Antibiotic Daptomycin by Hydrolytic Mechanisms," Antimicrob. Agents Chemo., 56(2), 757-764(2012).   DOI
41 Wang, P., Kim, W., Pickens, L. B., Gao, X. and Tang, Y., "Heterologous Expression and Manipulation of Three Tetracycline Biosynthetic Pathways," Angew. Chem. Int. Ed., 51, 11136-11140 (2012).   DOI   ScienceOn
42 Khmelnitski, Y. L., Budde, C., Arnold, J. M., Usyatinsky, A., Clark, D. S. and Dordick, J. S., "Synthesis of Water Soluble Paclitaxel Derivatives by Enzymatic Acylation," J. Am. Chem. Soc. 119, 11554-11555(1997).   DOI   ScienceOn
43 Loncaric, C., Merriweather, E. and Walker, K. D., "Profiling a Taxol Pathway 10-acetyltransferase: Assessment of the Specificity and the Production of Baccatin III by in vivo Acetylation in E. coli," Chem. Biol., 13, 309-317(2006).   DOI   ScienceOn
44 Longa, R. M., Lagisetti, C., Coates, R. M. and Croteaua, R. B., "Specificity of the N-benzoyl Transferase Responsible for the Last Step of Taxol Biosynthesis," Arch. Biochem. Biophys., 477(2), 384-389(2008).   DOI   ScienceOn
45 Nevarez, D. M., Mengistu, Y. A., Nawarathne, I. N. and Walker, K. D., "An N-aroyltransferase of the BAHD Superfamily has Broad Aroyl CoA Specificity in vitro with Analogues of N-dearoylpaclitaxel," J. Am. Chem. Soc., 131(16), 5994-6002(2009).   DOI   ScienceOn
46 Pickens, L. B., Kim, W., Wang, P., Zhou, H., Watanabe, K., Gomi, S. and Tang, Y., "Biochemical Analysis of the Biosynthetic Pathway of an Anticancer Tetracycline SF2575," J. Am. Chem. Soc., 131, 17677-17689(2009).   DOI   ScienceOn
47 Adamczyk, M., Gebler, J. C. and Mattingly, P. G., "Lipase Mediated Hydrolysis of Rapamycin. 42-hemisuccinate Benzyl and Methyl Esters," Tetrahedron Lett., 35, 1019-1022(1994).   DOI   ScienceOn
48 Storz, T., Gu, J., Wilk, B. and Olsen, E., "Regioselective Lipasecatalyzed Acylation of 41-desmethoxy-rapamycin Without Vinyl Esters," Tetrahededron Lett., 51, 5511-5515(2010).   DOI   ScienceOn
49 Wang, P., Gao, X. Chooi, Y. H., Deng, Z. and Tang, Y., "Genetic Characterization of Enzymes Involved in the Priming Steps of Oxytetracycline Biosynthesis in Streptomyces rimosus," Microbiol., 157(8), 2401-2409(2011).   DOI   ScienceOn
50 Pickens, L. B., Sawaya, M. R., Rasool, H., Pashkov, I., Yeates, T. O. and Tang, Y., "Structural and Biochemical Characterization of the Salicylyl-acyltranferase SsfX3 from a Tetracycline Biosynthetic Pathway," J. Biol. Chem., 286, 41539-41551(2011).   DOI
51 Gonzalez-Sabin, J., Moran-Ramallal, R. and Rebolledo, F., "Regioselective Enzymatic Acylation of Complex Natural Products: Expanding Molecular Diversity," Chem. Soc. Rev., 40, 5321-5335(2011).   DOI   ScienceOn
52 Mortison, J. D. and Sherman, D. H., "Frontiers and Opportunities in Chemoenzymatic Synthesis," J. Org. Chem., 75(21), 7041-7051 (2010).   DOI   ScienceOn
53 Minowa, Y. Araki, M. and Kanehisa, A., "Comprehensive Analysis of Distinctive Polyketide and Nonribosomal Peptide Structural Motifs Encoded in Microbial Genomes," J. Mol. Biol., 368, 1500-1517(2007).   DOI   ScienceOn
54 Zhou, H., Xie, X. and Tang, Y., "Engineering Natural Products Using Combinatorial Biosynthesis and Biocatalysis," Curr. Opin. Biotechnol., 19, 590-596(2008).   DOI   ScienceOn
55 Lee, S. Y., Kim, H. U., Park, J. H., Park, J. M. and Kim, T. Y., "Metabolic Engineering of Microorganisms: General Strategies and Drug Production," Drug Discov. Today, 14, 78-88(2009).   DOI   ScienceOn
56 Chooi, Y. H. and Tang, Y., "Navigating the Fungal Polyketide Chemical Space: from Genes to Molecules," J. Org. Chem., 77, 99339953(2012).   DOI   ScienceOn
57 Zabala, A, O., Cacho, R, A. and Tang, Y., "Protein Engineering Towards Natural Product Synthesis and Diversification," J. Ind. Microbiol. Biotechnol., 39, 227-241(2012).   DOI
58 Truman, A. W., Dias, M. V. B., Wu, S., Blundell, T. L., Huang, F. and Spencer, J. B., "Chimeric Glycosyltransferases for the Generation of Hybrid Glycopeptides," Chem. Biol., 16, 676-685(2009).   DOI   ScienceOn
59 Marienhagen, J. and Bott, M., "Metabolic Engineering of Microorganisms for the Synthesis of Plant Natural Products," J. Biotechnol., 163, 166-178(2013).   DOI   ScienceOn
60 Pickens, L. B., Tang, Y. and Chooi, Y. T., "Metabolic Engineering for the Production of Natural Products," Ann. Rev. Chem. Biomol. Eng., 2, 211-236(2011).   DOI
61 Dunn, B. J. and Khosla, C., "Engineering the Acyltransferase Substrate Specificity of Assembly Line Polyketide Synthases," J. R. Soc. Interface, 29 May 2013: 20130297.
62 Michels, P. C., Khmelnitsky, Y. L., Dordick, J. S. and Clark, D. S., "Combinatorial Biocatalysis: a Natural Approach to Drug Discovery," Trends Biotechnol., 16(5), 210-215(1998).   DOI   ScienceOn
63 Gross, R. A., Ganesh, M. and Lu, W., "Enzyme-catalysis Breathes New Life Into Polyester Condensation Polymerizations," Trends Biotechnol., 28, 435-443(2010).   DOI   ScienceOn
64 Park, H. G., Do., J. H. and Chang, H. N., "Regioselective Enzymatic Acylation of Multi-hydroxyl Compounds in Organic Synthesis," Biotech. Bioproc. Eng., 8, 1-8(2003).   DOI   ScienceOn
65 Jadhav, S. R., Vemula, P. K., Kumar, R., Raghavan, S. R. and John, G., "Sugar-serived Phase-selective Molecular Gelators as Model Solidifiers for Oil Spills," Angew. Chem. Int. Ed., 49, 7695-7698 (2010).   DOI   ScienceOn
66 Park, O. J., Jeon, G. J. and Yang, J. W., "Protease-catalyzed Synthesis of Disaccharide Amino Acid Esters in Organic Media," Enz. Microb. Technol., 25, 455-462(1999).   DOI   ScienceOn
67 Park, O. J., Kim, D. Y. and Dordick, J. S., "Enzyme-catalyzed Synthesis of Sugar-sontaining Monomers and Linear Polymers," Biotechnol. Bioeng., 70, 208-216(2000).   DOI   ScienceOn
68 John, G., Zhu, G., Li, J. and Dordick, J. S., "Enzymatically Derived Sugar-containing Self-assembled Organogels with Sanostructured Morphologies," Angew. Chem. Int. Ed., 45, 4772-4775(2006).   DOI   ScienceOn
69 Jiang, Y., Morley, K. L., Schrag, J. D. and Kazlauskas, R. J., "Different Active-site Loop Orientation in Serine Hydrolases Versus Acyltransferases," ChemBioChem, 12, 768-776(2011).   DOI   ScienceOn
70 Brenneis, R. and Baeck, B., "Esterification of Fatty Acids Using Candida antarctica Lipase A in Water-abundant Systems," Biotechnol. Lett., 34, 1459-1463(2012).   DOI   ScienceOn
71 Neang, P. M., Subileau, M., Perrier, V. and Dubreucq, E., "Peculiar Features of Four Enzymes of the CaLA Superfamily in Aqueous Media: Differences in Substrate Specificities and Abilities to Catalyze Alcoholysis," J. Mol. Cat. B: Enz., 94, 36-46(2013).   DOI   ScienceOn
72 Xie, X. and Tang, Y., "Efficient Synthesis of Simvastatin by Use of Whole-cell Biocatalysis," Appl. Environ. Microbiol., 73, 2054-2060(2007).   DOI   ScienceOn
73 Gao, X., Xie, X., Pashkov, I., Sawaya, M. R., Laidman, J., Zhang, W., Cacho, R., Yeates, T. O. and Tang, Y., "Directed Evolution and Structural Characterization of a Simvastatin Synthase," Chem. Biol., 16, 1064-1074(2009).   DOI   ScienceOn
74 Barbayianni, E. and Kokotos, G., "Biocatalyzed Regio- and Chemoselective Ester Cleavage: Synthesis of Bioactive Molecules," ChemCatChem, 4, 592-608(2012).   DOI
75 Collier, S., "Commercial Biocatalytic Processes to Simvastatin and Other Molecules," Org. Proc. Res. Dev., Barcelona, Spain, Scientific Update(2010).
76 Paravidino, M. and Hanefeld, U., "Enzymatic Acylation: Assessing the Greenness of Different Acyl Donors," Green Chem., 2651-2657(2011).
77 Sheldon, R. A., "The E Factor: Fifteen Years on," Green Chem., 9, 1273-1283(2007).   DOI   ScienceOn
78 Schoevaart, R. et al., "Chiral Technology: Industrial Biocatalysis with Standard Hydrolytic Bulk Enzymes," Spec. Chem. Mag., 27(8), 38(2007).
79 Miyazawa, K. and Yoshida, N., "Process for Producing Optically Active $\alpha$-hydroxyesters Using Lipase PS," UP 5248610 (Chisso, Japan) (1993).
80 Kobayashi, S., "Enzymatic Polymerization," Encyc. Polym. Sci. Tech., 2011.
81 Kobayashi, S., "Recent Developments in Lipase-catalyzed Synthesis of Polyesters," Macromol. Rapid Comm., 30, 237-266(2009).   DOI   ScienceOn
82 OECD Primer, "The Application of Biotechnology to Industrial Sustainability-a Primer," Organization for Economic Co-operation and Development (OECD), 2001.
83 Binns, F. and Taylor, A., "Enzymatic Synthesis," WO 1994012652 (Baxenden Chemicals, UK) (1994).
84 Takashi Kobayashi, Lipase-catalyzed syntheses of sugar esters in non-aqueous media, Biotechnol. Lett., 33(10), 1911-1919(2011).   DOI   ScienceOn
85 Binns, F., Harffey, P., Roberts, S. M. and Taylor, A., "Studies of Lipase-catalyzed Polyesterification of An Unactivated Diacid/diol System," J. Pol. Sci. Pol. Chem. A, 36(12), 2069-2079(1998).   DOI