Comparison between Glucoamylase and ƒ -Glucosidase Seiya CHIBA Department of Agricultural Chemistry, Faculty of Agriculture, Hokkaido University (Nish

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1 Comparison between Glucoamylase and ƒ -Glucosidase Seiya CHIBA Department of Agricultural Chemistry, Faculty of Agriculture, Hokkaido University (Nishi 9, Kita 9, Kita-ku, Sapporo 060, Japan) The difference between glucoamylase [EC exo-1, 4-ƒ -D-glucosidase] and ƒ -glucosidase [EC ƒ -glucosidase] was discussed on the basis of the kinetic parameters, Km, ko(- V/eo; eo, enzyme concentration), and ko/km, for maltooligosaccharides. In glucoamylase, there is a large difference between the ko values of maltose and those of other maltooligosaccharides. In ƒ -glucosidases, however, the ko values are little dependent on the degree of polymerization of glucosyl residues in a series of maltooligosaccharides. The active site of ƒ -glucosidase, like glucoamylase, have been also considered to be made up by the subsite structure. The subsite affinities of three kinds of glucoamylases were compared with those of five kinds of ƒ -glucosidases from various origins. The difference in the substrate specificities between glucoamylase and a- glucosidase was reasonably interpreted by their subsite affinities. In the "Enzyme Nomenclature," the distinction between glucoamylase and a group of ƒ - glucosidases capable of attacking ƒ -glucan is not always clear, that is, lysosomal a-glucosidase and acid maltase, which usually mean mammalian acid ƒ -glucosidase, are classified into the category of EC However, it has been reported that the acid a-glucosidases from pig liver and rabbit muscle also produce ƒ -glucose. Glucoamylase can be definitely distinguished from ƒ - glucosidase in their anomeric forms of the product glucose: the former releases J3-anomer, and the latter releases a-anomer. Therefore, it appears to be not proper that certain kinds of ƒ - glucosidase are included in the group of EC , and also that the trivial name recommended for glucoamylase is exo-1, 4-ƒ -D-glucosidase. The term glucoamylase itself may be more proper for the trivial name. The reaction mechanisms of glucoamylase and ƒ -glucosidase were proposed, by which the mechanisms of hydrolysis, transglucosylation and reverse reaction were discussed. Moreover, the reason why the configuration of the carbonyl carbon of the product glucose is retained or inverted was explained.

2 ~~ hil Fig. 1. Reaction scheme of glucoamylase (A) and a-glucosidase (B). Broken line is the splitting point. R: reducing side residue or aglycone. H-OA: acceptor. Table 1. Kinetic parameters of Rhizopus deleinar, Rhizopus niveus varioti glucoamylases., 4) and Paecilomyces Rh. delemar: reaction, 25 Ž, ph 4.5; M. W., 7.0 x 104. Rh. niveus: reaction, 25 Ž, ph 4.5; M. W., 6.0 x 104. P, varioti: reaction, 37 Ž, ph 4.5; M. W., 6.9 ~ 104. Molecular activity ko is expressed as V/eo, where V is the maximum velocity for the cleavage of a- glucosidic bond of nonreducing terminal, and eo, the concentration of enzyme. G2, G3, c, G7: maltose, maltotriose,., maltoheptaose.

3 Fig. 2. Histograms showing the subsite affinities of Rhizopus delemar, Rhizopus niveus, and Paecilomyces varioti glucoamylases. The wedge indicates the catalytic site. Table 2. Kinetic parameters of brewer's yeast a-glucosidase U. Reaction, 33 Ž, ph 6.8; M. W., 7.0 x 104. * Theoretically calculated values from the subsite affinities ƒó G: phenyl a-glucoside..

4 Table 3. Kinetic parameters of honey bee8) and Saccharomyces logos9) a-glucosidases. Honey bee: reaction, 35 Ž, ph 5.0; M. W., 9.8 x 104. Sacch, logos: reaction, 33 Ž, ph 4.6; M. W., 27x 104. Table 4. Kinetic parameters of honey bee8) and Takadiastase13) a-glucosidases. Takadiastase: reaction, 37 Ž, ph 4.0; M. W., 6.2 x 104. Honey bee: reaction 7.6x104. * mm of nonreducing terminal. SS: soluble starch., 35 Ž, ph 5.0; M. W., Table 5. Kinetic parameters of a-glucosidases from seeds of sweet corn, rice, and sugar beet. Sweet corn: reaction, 37 Ž, ph 3.6; M. W., 9.6 x 104. Rice( U) : reaction, 37 Ž, ph 4.0; M. W., 10 ~ 104. Sugar beet: reaction, 37 Ž, ph 4.5; M. W., 9.1 x 104. * mm of nonreducing terminal.

5 Table 6. Kinetic parameters of pig liver27 j and rabbit muscle28 j acid a-glucosidases. Pig liver: reaction, 37 Ž, ph 4.5; M. W., 10.7 x 104. Rabbit muscle: reaction 10.2 x 104., 37 C, ph 4.5; M. W., SG: shellfish glycogen. * mm of nonreducing terminal. Fig. 3. Histograms showing the subsite affinities of sweet corn seed, rice seed ( U), sugar beet seed, brewer's yeast ( U), and honey bee ( T) a-glucosidases.

6 Fig. 4. Procedures of gas-liquid chromatographic method for anomer analysis.

7 Fig. 5. Gas-liquid chromatograms of TMS-derivatives of products from 5 mm phenyl a-maltoside by honey bee a-glucosidase (A) and Rhizopus niveus glucoamylase (B). The chromatograms (A) and (B) indicate the products at 3 min and 2.7 min of reaction time, respectively. 1, arabitol (internal standard) ; 2, a-glucose; 3, a-glucose; 4, pheny a-glucoside; 5, phenyl a-maltoside. Table 7. Anomeric forms of the product glucose. M: phenyl a-maltoside.

8 Fig. 6. Reaction scheme of single replacement mechanism. BH: acidic group of enzyme. Table 8. Essential ionizable groups. Fig. 7. Reaction scheme of double replacement mechanism. B-: nucleophilic group of enzyme.

9 Fig. 8. A postulated mechanism of ƒ -glucosidase reaction. Fig. 9. A postulated mechanism of glucoamylase reaction.

10 of glucosyl- Fig. 10. A possible conformation intermediate. Downward arrow shows the direction of attack by water which gives /3-anomer, and upward arrow, a-anomer. 1) C. A. BUNTON, T. A. LEWIS, D. R. LLEWELLYN, H. TRISTAN and C. A. VERNON: Nature, 174, 560(1954); J. Chem. Soc., 1955, 4419(1955). 2) B. ZAGALK and H. CH. CURTIUS: Biochem. Biophys. Res. Commun., 62, 503(1975). 3) K. HIROMI, Y. NITTA, C. NUMATA and S. ONO: Biochim. Biophys. Acta, 302, 362(1973). 4) A. TANAKA, Y. FUKUCHI, M.OHNISHI, K. HIROMI, S. AIBARA and Y. MORITA: Agric. Biol. Chem., 47, 573(1983). 7) K. MATSUSAKA, S. CHIBA and T. SHIMOMURA: Agric. Biol. Chem., 41, 1917(1977). 8) S. TAKEWAKI, S. CHIBA, A. KIMURA, H. MATSUI and Y. KOIKE: Agric. Biol. Chem., 44, 731 (1980).

11 9) S. CHIBA, T. SAEKI and T. SHIMOMURA: Agric. Biol. Chem., 37, 1831(1973). 11) T. MATSUSHIMA: J. Biochem., 48, 138(1960). 12) S. SUGAWARA, Y. NAKAMURA and T. SHIMO MURA: Agric. Biol. Chem., 25, 358(1961). Vol. 4, 2nd ed., P. D. BOYER, H. LARDY and K. 14) H. MATSUI, I. YAZAWA and S. CHIBA: Agric. Biol. Chem., 45, 887(1981). 15) S. MURATA, H. MATSUI, S. CHIBA and T. SHIMOMURA: Agric. Biol. Chem., 43, 2131 (1979). 16) S. CHIBA, S. INOMATA, H. MATSUI and T. SHIMOMURA: Agric. Biol. Chem., 42, 241(1978). 17) S. CHIBA, N. HIBI and T. SHIMOMURA: Agric. Biol. Chem., 40, 1813(1976). 18) S. CHIBA, K. HIROMI, N. MINAMIURA, M. OHNISHI, T. SHIMOMURA, K. SUGA, T. SUGA NUMA, A. TANAKA, S. TOMIOKA and T. YAMAMOTO: J. Biochem., 85, 1135(1979). 19) S. ONO, K. HIROMI and Z. HAMAUZU: J. Biochem., 57, 34(1965). 20) J. E. G. BARNETT: Biochem. J., 123, 607(1971). 21) F. W. PARRISH and E. T. REESE: Carbohydr. Res., 3, 424(1967). 22) G. SEMENZA, C.-H. CURTIUS, J. KOLINSKA and M. MULLER: Biochem. Biophys. Acta, 146, 196 (1967). 23) J. OKUDA, I. MIWA, K. MAEDA and K. TOKUI: Carbohydr. Res., 58, 267(1977). 24) N. SHIOMI and J. YAMADA: Carbohydr. Res., 111, 175(1982). 25) S. CHIBA, A. KIMURA and H. MATSUI: Agric. Biol. Chem., 47, 1741(1983). 26) A. KIMURA and S. CHIBA: Agric. Biol. Chem., 47, 1747(1983). 27) H. MATSUI and S. CHIBA: Agric. Biol. Chem., 47, 707(1983). 28) H. MATSUI, M. SASAKI, E. TAKEMASA and S. CHIBA: J. Biochem., in press. 29) D. E. KOSHLAND, Jr.: in The Enzymes, Vol. 2, 2nd ed., P. D. BOYER, H. LARDY and K. MYRBACK, eds., Academic Press, Inc., New York, p. 305(1959). 30) K. KANAYA, S. CHIBA and T. SHIMOMURA: Agric. Biol. Chem., 43, 1841(1979). 31) H. MATSUI and S. CHIBA: Agric. Biol. Chem., 45, 141(1981). 32) H. MATSUI, T. YAMADA, Y. SOMEYA and S. CHIBA: Agric. Biol. Chem., 47, 1817(1983). 33) K. HIROMI, K. TAKAHASHI, Z. HAMAUZU and S. ONO: J. Biochem., 59, 469(1966). 34) D. M. BLOW and T. A. STEITZ: Ann. Rev. Biochem., 39, 63(1970). 35) F. C. MAYER and J. LARNER: J. Am. Chem. Soc., 81, 188(1959). 36) J. A. THOMA, J. E. SPRADLIN and S. DYGERT: in The Enzymes, Vol. 5, 3rd ed., P.D. BOYER, ed., Academic Press, Inc., New York, p. 115 (1971). 38) E. H. FISHER and E. A. STEIN: in The Enzymes, MYRBACK, eds., Academic Press, Inc., New York, p. 313(1960). 39) P. S. J. CHEETHAM: in Developments in Food Carbohydrate, Vol. 3, C. K. LEE and M. G. LINDLEY, eds., Applied Science Publishers, London and New Jersey, p. 107(1982).

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1) K. J. Laidler, "Reaction Kinetics", Vol. II, Pergamon Press, New York (1963) Chap. 1 ; P. G. Ashmore, "Catalysis and Inhibition of Chemical Reactio

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