Enzymatic synthesis of model substrates recognized by glucuronoyl esterases from Podospora anserina and Myceliophthora thermophila
详细信息 查看全文
- 作者：Constantinos Katsimpouras (1)
Ana?s Bénarouche (2)
David Navarro (2)
Michael Karpusas (3)
Maria Dimarogona (1)
Jean-Guy Berrin (2)
Paul Christakopoulos (4)
Evangelos Topakas (1) - 关键词：Glucuronoyl esterase ; Myceliophthora thermophila ; Podospora anserina ; Pichia pastoris ; Substrate specificity ; Aryl alkyl or alkenyl d ; glucuronates
- 刊名：Applied Microbiology and Biotechnology
- 出版年：2014
- 出版时间：June 2014
- 年：2014
- 卷：98
- 期：12
- 页码：5507-5516
- 全文大小：
- 参考文献：1. Aita GA, Salvi DA, Walker MS (2011) Enzyme hydrolysis and ethanol fermentation of dilute ammonia pretreated energy cane. Bioresour Technol 102(6):4444-448 CrossRef
2. Balakshin M, Capanema E, Gracz H, Chang HM, Jameel H (2011) Quantification of lignin-carbohydrate linkages with high-resolution NMR spectroscopy. Planta 233(6):1097-110 CrossRef
3. Bey M, Berrin J-G, Poidevin L, Sigoillot J-C (2011) Heterologous expression of / Pycnoporus cinnabarinus cellobiose dehydrogenase in / Pichia pastoris and involvement in saccharification processes. Microb Cell Fact 10:113 CrossRef
4. Blom N, Sicheritz-Ponten T, Gupta R, Gammeltoft S, Brunak S (2004) Prediction of post-translational glycosylation and phosphorylation of proteins from the amino acid sequence. Proteomics 4:1633-649 CrossRef
5. Bounias M (1980) N-(1-naphthyl)ethylenediamine dihydrochloride as a new reagent for nanomole quantification of sugars on thin-layer plates by a mathematical calibration process. Anal Biochem 106(2):291-95 CrossRef
6. Cantarel BL, Coutinho PM, Rancurel C, Bernard T, Lombard V, Henrissat B (2009) The carbohydrate-active enzymes database (CAZy): an expert resource for glycogenomics. Nucleic Acids Res 37:D233–D238 CrossRef
7. Charavgi MD, Dimarogona M, Topakas E, Christakopoulos P, Chrysina ED (2013) The structure of a novel glucuronoyl esterase from / Myceliophthora thermophila gives new insights into its role as a potential biocatalyst. Acta Crystallogr D Biol Crystallogr 69(Pt 1):63-3 CrossRef
8. Choi JW, Choi D-H, Faix O (2007) Characterization of lignin–carbohydrate linkages in the residual lignins isolated from chemical pulps of spruce ( / Picea abies) and beech wood ( / Fagus sylvatica). J Wood Sci 53:309-13 CrossRef
9. de Graaf M, Nevalainen TJ, Scheeren HW, Pinedo HM, Haisma HJ, Boven E (2004) A methylester of the glucuronide prodrug DOX-GA3 for improvement of tumor-selective chemotherapy. Biochem Pharmacol 68(11):2273-281 CrossRef
10. ?uranová M, Hirsch J, Kolenová K, Biely P (2009a) Fungal glucuronoyl esterases and substrate uronic acid recognition. Biosci Biotechnol Biochem 73:2483-487 CrossRef
11. ?uranová M, Spanikova S, Wosten HAB, Biely P, de Vries RP (2009b) Two glucuronoyl esterases of / Phanerochaete chrysosporium. Arch Microbiol 191:133-40 CrossRef
12. Gasteiger E, Hoogland C, Gattiker A, Duvaud S, Wilkins MR, Appel RD, Bairoch A (2005) Protein identification and analysis tools on the ExPASy server. In: Walker JM (ed) The proteomics protocols handbook. Humana Press, New Jersey, pp 571-07 CrossRef
13. Gibson LJ (2012) The hierarchical structure and mechanics of plant materials. J R Soc Interface 9(76):2749-766 CrossRef
14. Hirsch J, Koo? M, Ková? P (1998) Improved synthesis of an aldobiouronic acid related to hardwood xylans, and preparation of a derivative thereof suitable for linking to proteins. Carbohydr Res 310:145-49 CrossRef
15. Hori C, Gaskell J, Igarashi K, Samejima M, Hibbett DS, Henrissat B, Cullen D (2013) Genomewide analysis of polysaccharides degrading enzymes in 11 white- and brown-rot Polyporales provides insight into mechanisms of wood decay. Mycologia 105(6):1412-427 CrossRef
16. Humphrey W, Dalke A, Schulten K (1996) VMD: visual molecular dynamics. J Mol Graph 14(1):33-8, 27-28 CrossRef
17. Karnaouri AC, Topakas E, Christakopoulos P (2014) Cloning, expression, and characterization of a thermostable GH7 endoglucanase from / Myceliophthora thermophile capable of high-consistency enzymatic liquefaction. Appl Microbiol Biotechnol 98(1):231-42 CrossRef
18. Laemmli UK (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227:680-85 CrossRef
19. Li X-L, ?pániková S, de Vries RP, Biely P (2007) Identification of genes encoding microbial glucuronoyl esterases. FEBS Lett 581:4029-035 CrossRef
20. Moreau B, Lognay GC, Blecker C, Brohee JC, Chery F, Rollin P, Paquot M, Marlier M (2004) Synthesis of novel d -glucuronic acid fatty esters using / Candida antarctica lipase in tert-butanol. Biotechnol Lett 26(5):419-24 CrossRef
21. Otto RT, Bornscheuer UT, Scheib H, Pleiss J, Syldatk C, Schmid RD (1998) Lipase-catalyzed esterification of unusual substrates: synthesis of glucuronic acid and ascorbic acid (vitamin C) esters. Biotechnol Lett 20(11):1091-094 CrossRef
22. Petersen TN, Brunak S, von Heijne G, Nielsen H (2011) SignalP 4.0: discriminating signal peptides from transmembrane regions. Nat Methods 8:785-86 CrossRef
23. Pokkuluri PR, Duke NE, Wood SJ, Cotta MA, Li XL, Biely P, Schiffer M (2011) Structure of the catalytic domain of glucuronoyl esterase Cip2 from / Hypocrea jecorina. Proteins 79(8):2588-592 CrossRef
24. Ralph J, Hatfield RD, Piquemal J, Yahiaoui N, Pean M, Lapierre C, Boudet AM (1998) NMR characterization of altered lignins extracted from tobacco plants down-regulated for lignification enzymes cinnamylalcohol dehydrogenase and cinnamoyl-CoA reductase. PNAS 95(22):12803-2808 CrossRef
25. Sarkanen KV (1971) In: Sarkanen KV, Ludwig CH (eds) Lignins: occurrence, formation, structure and reactions. Wiley-Interscience, New York, pp 95-63
26. ?pániková S, Biely P (2006) Glucuronoyl esterase–novel carbohydrate esterase produced by / Schizophyllum commune. FEBS Lett 580(19):4597-601 CrossRef
27. ?pániková S, Polakova M, Joniak D, Hirsch J, Biely P (2007) Synthetic esters recognized by glucuronoyl esterase from / Schizophyllum commune. Arch Microbiol 188(2):185-89 CrossRef
28. Steentoft C, Vakhrushev SY, Joshi HJ, Kong Y, Vester-Christensen MB, Schjoldager KT, Lavrsen K, Dabelsteen S, Pedersen NB, Marcos-Silva L, Gupta R, Bennett EP, Mandel U, Brunak S, Wandall HH, Levery SB, Clausen H (2013) Precision mapping of the human / O-GalNAc glycoproteome through SimpleCell technology. EMBO J 32(10):1478-488 CrossRef
29. Stoscheck CM (1990) Quantification of protein. Methods Enzymol 182:50-8 CrossRef
30. Topakas E, Moukouli M, Dimarogona M, Vafiadi C, Christakopoulos P (2010) Functional expression of a thermophilic glucuronyl esterase from / Sporotrichum thermophile: identification of the nucleophilic serine. Appl Microbiol Biotechnol 87(5):1765-772 CrossRef
31. Tsai AYL, Canam T, Gorzsas A, Mellerowicz EJ, Campbell MM, Master ER (2012) Constitutive expression of a fungal glucuronoyl esterase in / Arabidopsis reveals altered cell wall composition and structure. Plant Biotechnol J 10:1077-087 CrossRef
32. Vafiadi C, Topakas E, Biely P, Christakopoulos P (2009) Purification, characterization and mass spectrometric sequencing of a thermophilic glucuronoyl esterase from / Sporotrichum thermophile. FEMS Microbiol Lett 296:178-84 CrossRef
33. Wong DWS, Chan VJ, McCormack AA, Hirsch J, Biely P (2012) Functional cloning and expression of the / Schizophyllum commune glucuronoyl esterase gene and characterization of the recombinant enzyme. Biotechnol Res Inter vol. 2012, article ID 951267, doi:10.1155/2012/951267
34. Wymelenberg AV, Gaskell J, Mozuch M, Sabat G, Ralph J, Skyba O, Mansfield SD, Blanchette RA, Martinez D, Grigoriev I, Kersten PJ, Cullen D (2010) Comparative transcriptome and secretome analysis of wood decay fungi / Postia placenta and / Phanerochaete chrysosporium. Appl Environ Microbiol 76:3599-610 CrossRef - 作者单位：Constantinos Katsimpouras (1)
Ana?s Bénarouche (2)
David Navarro (2)
Michael Karpusas (3)
Maria Dimarogona (1)
Jean-Guy Berrin (2)
Paul Christakopoulos (4)
Evangelos Topakas (1)
1. Biotechnology Laboratory, School of Chemical Engineering, National Technical University of Athens, 5 Iroon Polytechniou Str., Zografou Campus, Athens, 15780, Greece
2. INRA, Aix Marseille Université, UMR1163, Polytech Marseille, 13288, Marseille, France
3. Physics Laboratory, Department of Biotechnology, Agricultural University of Athens, Athens, 11855, Greece
4. Biochemical and Chemical Process Engineering, Division of Sustainable Process Engineering, Department of Civil, Environmental and Natural Resources Engineering, Lule? University of Technology, 97187, Lule?, Sweden - ISSN：1432-0614
文摘
Glucuronoyl esterases (GEs) are recently discovered enzymes that are suggested to cleave the ester bond between lignin alcohols and xylan-bound 4-O-methyl-d-glucuronic acid. Although their potential use for enhanced enzymatic biomass degradation and synthesis of valuable chemicals renders them attractive research targets for biotechnological applications, the difficulty to purify natural fractions of lignin-carbohydrate complexes hampers the characterization of fungal GEs. In this work, we report the synthesis of three aryl alkyl or alkenyl d-glucuronate esters using lipase B from Candida antarctica (CALB) and their use to determine the kinetic parameters of two GEs, StGE2 from the thermophilic fungus Myceliophthora thermophila (syn. Sporotrichum thermophile) and PaGE1 from the coprophilous fungus Podospora anserina. PaGE1 was functionally expressed in the methylotrophic yeast Pichia pastoris under the transcriptional control of the alcohol oxidase (AOX1) promoter and purified to its homogeneity (63?kDa). The three d-glucuronate esters contain an aromatic UV-absorbing phenol group that facilitates the quantification of their enzymatic hydrolysis by HPLC. Both enzymes were able to hydrolyze the synthetic esters with a pronounced preference towards the cinnamyl-d-glucuronate ester. The experimental results were corroborated by computational docking of the synthesized substrate analogues. We show that the nature of the alcohol portion of the hydrolyzed ester influences the catalytic efficiency of the two GEs.