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Carbohydrate Epimerase の触媒作用, 構造, その応用例

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Carbohydrate Epimerase の触媒作用, 構造, その応用例 1 J. Appl. Glycosci., 57,1―6 (2010) !C 2010 The Japanese Society of Applied Glycoscience Review Catalysis, Structures, and Applications of Carbohydrate Epimerases (Received July 10, 2009; Accepted August 23, 2009) Susumu Ito1,＊ 1Department of Bioscience and Biotechnology, Faculty of Agriculture, University of the Ryukyus (1, Senbaru, Nishihara-cho, Okinawa 903 ―0213, Japan) Abstract: More than 20 types of carbohydrate epimerase have been reported to date. Distinctly different en- zymes recognize the C1, C2, C3, C4, C5 or C6 position of carbohydrate substrates. They include, for instance, aldose 1-epimerase, N-acetyl-D-glucosamine 2-epimerase, UDP-N-acetylglucosamine 2-epimerase, cellobiose 2- epimerase, D-ribulose-5-phosphate 3-epimerase, L-ribulose-5-phosphate 4-epimerase, UDP-galactose 4- epimerase, dTDP-6-deoxy-D-xylo-4-hexulose 3,5-epimerase, GDP-mannose 3,5-epimerase and ADP-L-glycero-D- mannoheptose 6-epimerase. Their biological properties, catalytic mechanisms and tertiary structures are very diverse. This review focuses on the catalysis, structures and applications of carbohydrate epimerases that have recently been characterized in detail. Key words: carbohydrate epimerase, catalytic property, reaction mechanism, application Metabolisms of carbohydrates proceed via many kinds glucosamine 2-epimerase (EC 5.1.3.8), UDP-N -acetyl- of enzymes which catalyze oxidation, reduction, dehydra- glucosamine 2-epimerase (EC 5.1.3.14), cellobiose 2-epi- tion, acetylation and epimerization. Carbohydrates fulfill merase (EC 5.1.3.11), D-ribulose-5-phosphate 3-epimerase many biological roles in all living cells, such as energy (EC 5.1.3.1), L-ribulose-5-phosphate 4-epimerase (EC source, structural elements and molecular recognition 5.1.3.4), UDP-galactose 4-epimerase (EC 5.1.3.2), dTDP- markers and are used as precursors for the biosynthesis of 6-deoxy-D-xylo-4-hexulose 3,5-epimerase (EC 5.1.3.13), cellular building blocks.1) GDP-mannose 3,5-epimerase (EC 5.1.3.18) and ADP-L- Epimerase is a member of isomerases, which catalyze glycero-D-mannoheptose 6-epimerase (EC 5.1.3.20). Ac- the inversion of stereochemistry in biological (or syn- cording to Allard et al .,1) the reaction mechanism of car- thetic) molecules. Carbohydrate epimerases catalyze the bohydrate epimerases can be divided into four types, reversible interconversion of carbohydrates.1,2) There are which involve 1) transient keto intermediate (UDP- many reports on the enzymatic properties, genes, location galactose 4-epimerase and ADP-L-glycero-D-manno- in metabolic pathways and sources of carbohydrate epi- heptose 6-epimerase), 2) protonation／deprotonation (GDP- merases (http:／／www.expasy.org／enzyme／; http:／／brenda mannose 3,5-epimerase), 3) nucleotide elimination and re- -enzymes.org／; http:／／www.find-health-articles.com／msh_ addition (UDP-N-acetylglucosamine 2-epimerase)or4)C- 20-carbohydrate-epimerases.htm). The enzymes have been C bond cleavage (L-ribulose-5-phosphate 4-epimerase). targeted for antimicrobial drug designs in order to create For these several years, detailed tertiary structures and／or new agents against infectious diseases in humans.1,3―6) reaction mechanisms of carbohydrate epimerases have However, there have been few reports on commercial ap- been reported in the literature. plications of carbohydrate epimerases to date. In this re- view, I focus on recent topics concerning the enzymes 1. N-Acetyl-D-glucosamine 2-epimerase (AGE). with respect to their catalytic properties and structures and In bacteria, some orthologs in the genomes of photo- to production of bioactive mono- and oligosaccharides synthetic cyanobacteia have been annotated as AGE. The and bioethanol. tertiary structure of an AGE from Anabaena sp. CH1 (aAGE; PDB code 2gz6) was solved and shown to be a Catalytic properties and structures of carbohydrate homodimer having an (α／α)6 barrel core structure by Lee epimerases. et al .7) (see Fig. 2). Together with the microenvironment More than 20 types of carbohydrate epimerase have around active-site cleft, the residues Arg57, His239, Glu been reported to date. Usually, the C1, C2, C3, C4, C5 242, Glu308, His372 and Arg375 were shown to be re- and C6 positions of free or substituted mono- and oligo- quired for activity by site-directed mutagenesis experi- saccharides are recognized by distinctly different enzymes, ments. The reversible epimerization at the C2 position of such as aldose 1-epimerase (EC 5.1.3.3), N-acetyl-D- GlcNAc is mediated by the conserved residues His239 (deprotonation) and His372 (protonation) as the acid／base ＊ Corresponding author (Tel.／Fax. +81―98―895―8804, E-mail: sito catalysts. @agr.u-ryukyu.ac.jp). In mammalian cells, the physiological role of AGE had Abbreviations: AGE, N-acetyl-D-glucosamine 2-epimerase; CE, been suggested to be the regulation of the renin- cellobiose 2 epimerase; RaCE, CE from Ruminococcus albus; - angiotension system because high activity was found in RmlC, dTDP-6-deoxy-D-xylo-4-hexulose 3,5-epimerase; DTE, D- tagatose 3-epimerase; DPE, D-psicose 3-epimerase; aAGE, AGE pigs, rats and humans, and the porcine kidney enzyme 8) from Anabaena sp.; Neu5A, N-acetylneuraminic acid. had renin-binding activity. However, other studies sug- 2 J. Appl. Glycosci., Vol. 57, No. 1 (2010) gest that AGE functions primarily as the enzyme for the or mannose moiety of cello-oligosaccharides, lactose, β- conversion of ManNAc to GlcNAc and plays a key role mannobiose (4-O-β-D-mannopyranosyl-D-mannose) and in sialic acid metabolism.9,10) globotriose [O-α-D-galactopyranosyl-(1→4)-O-β-D-galacto- pyranosyl-(1→4)-D-glucose]. The products from lactose, 2. Cellobiose 2-epimerase (CE). β-mannobiose and globotriose are epilactose (4-O- CE from Ruminococcus albus (RaCE) has also been β-D-galctopyranosyl-D-mannose), 4-O-β-D-mannopyranosyl- suggested to have a basal core structure of an (α／α)6 bar- D-glucose and O -α-D-galactopyranosyl-(1→4)-O -β-D- rel, as judged by the secondary structure prediction and galactopyranosyl-(1→4)-D-mannose, respectively (see structure-based alignment with AGEs.11) The residues Arg Fig. 3). The products from cello-oligosaccharides were as- 52, Phe114, His243, Glu246, Trp249, Trp303, Trp304, signed to the corresponding 2-epimerized products. The Glu308, His374 and Arg377 were determined to be re- equilibrium ratio between lactose and epilactose was ap- quired for activity by site-directed mutagenesis,12) as proximately 60:40. Cellobitol, lactitol, N-acetyl-D- shown in Fig. 1. Like in aAGE, His243 and His374 were glucosamine, N-acetyl-D-mannosamine and N-acetyl- assigned to serve as the active site acid／base catalysts be- lactosamine did not serve as substrates. At present, func- cause RaCE has no activity around pH 5. This mechanis- tional CEs have been reported to occur only in bacte- 11,13,15,16) tic proposal is supported by the pKa value of His (around ria, and their physiological role(s) has not been 6.3) in comparison with those of Glu and Asp (around clarified yet. They share less than 20% identity to aAGE,7) 4.1). CE reactions may also involve a protonation／depro- and no homology was observed with the other hetero- tonation step. gonous epimerases. CE was first found in the culture fluid of the anaerobic ruminal bacterium, R. albus 7 (ATCC 27210T).13) It cata- 3. Mannose 2-epimerase activity. lyzes the reversible epimerization of cellobiose to 4-O -β- Centeno et al .17) reported that CmEpiA, formerly desig- D-glucopyranosyl-D-mannose. Recently, we purified RaCE nated Unk2 (AAS19694) of unknown function in the from R. albus NE1 cells and sequenced the encoding Cellvibrio mixtus genome, had a weak epimerization ac- gene for the first time.11,14) We also reported the gene se- tivity at the C2 position of mannose, generating glucose. quences and catalytic properties of CEs from Eubacterium The four possible catalytic residues are well conserved as cellulosolvens 15) and Bacteroides fragilis cells.16) Unlike Arg63, His256, Glu324 and His389. However, the phylo- AGE, the CEs appear to exist as a monomeric form under genetic position of CmEpiA is on a branch different from defined conditions. They catalyzed a hydroxyl stereoisom- those of CEs.16) CE can 2-epimerize β-mannobiose but has erism at the C2 positions of the reducing terminal glucose no activity toward mannose. 4. dTDP-6-deoxy-D-xylo-4-hexulose 3,5-epimerase (RmlC). RmlC epimerizes both the C3′and C5′positions of dTDP-6-deoxy-D-xylo-4-hexulose , yielding dTDP-6- deoxy-L-lyxo-4-hexulose. The enzyme in Streptococcus suis (PDB code 2ixl) requires a conserved His as the base and a conserved Tyr as the acid.18) Recent study with the RmlC from Pseudomonas aeruginosa (PDB code 2ixi); clarifies that the enzyme has a double-stranded β-helix structure, as shown in Fig. 2, and uses the conserved Tyr 134 and His65 as the acid／base catalysts, where the epimerization at C5′proceed faster than that at C3′.4) L-Rhamnose is commonly found in glycoconjugates of bacteria, including pathogenic ones, and neither the sugar nor the enzymes required for the rhamnose biosynthesis are found in humans. RmlC is involved in the dTDP-L- rhamnose biosynthetic pathway that converts glucose-1- phosphate to dTDP-L-rhamnose.19) 5. D-Tagatose 3-epimerase (DTE) and D-psicose 3- epimerase (DPE). DTE catalyzes the reversible epimerization of various ketohexoses at the C3 position, and many DTEs have Fig. 1. A model structure and possible catalytic amino-acid resi- been characterized from various sources (AAL45542, AL dues of the R. albus CE (RaCE). 93912b, BAB50266, BX294153, F72381, NC_005126, The model structure of RaCE was constructed with porcine kid- NP_435986, NP_865388). DTE family enzymes catalyze 12) ney AGE (PDB code 1fp3) as a template.
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