Synthesis and characterization of new chromogenic substrates for exoglycosidases: a-glucosidase, a-mannosidase, and b-galactosidase

Glycosides of 4-nitrocatechol (1,2-dihydroxy 4-nitrobenzene) with a-D-glucopyranose and a-D-mannopyranose were synthesized by the glycosylation of phenol with peracetylated sugars in the presence of BF3\cdot OBu2. The glycoside of 4-nitrocatechol with b-D-galactopyranose was prepared by the glycosylation of this phenol as sodium phenoxide with tetra-O-benzoyl-a-D- galactopyranosyl bromide. The structure of the reaction products was confirmed by 1 H and 13C NMR spectra and by chemical analysis. The latter consisted of acidic hydrolysis, followed by ethyl ether extraction and colorimetric determination of 4-nitrocatechol in the ether phase and application of the anthrone method for the sugar in the water phase. The synthetic glycosides were tested as substrates for enzymes from animal, vegetal, and microbial materials.

Anahtar Kelimeler:

Glycosylation, 4-nitrocatechol-glycoside, exoglycosidase, enzymatic substrate

Synthesis and characterization of new chromogenic substrates for exoglycosidases: a-glucosidase, a-mannosidase, and b-galactosidase

Keywords:

Glycosylation, 4-nitrocatechol-glycoside, exoglycosidase, enzymatic substrate,

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Robinson, D.; Smith, J. N.; Williams, R. T. Biochem. J. 1951, 49, lxxiv.
Robinson, D.; Smith, J. N.; Spencer, B.; Williams, R. T. Biochem. J. 1952, 51, 202–208.
Farooqui, A. A. Clin. Chim. Acta 1980, 100, 285–299.
Folkman, M. J.; Chen, N. T.; Corey, E. J. United States Patent 5096892/1992.
Rip, J. W.; Gordon, B. A. Clin. Biochem. 1998, 31, 29–31.
Aizawa, K. Enzymologia 1939, 6, 321–324.
Huggins, C.; Smith, D. R. J. Biol. Chem. 1947, 170, 391–398.
Norris, A. J.; Whitelegge, J. P.; Yaghoubian, A.; Alattia, J.-R.; Priv´e, G. G.; Toyokuni, T.; Sun, H.; Brooks, M. N.; Panza, L.; Matto, P.; Compostella, F.; Remmel, N.; Klingenstein, R.; Sandhoﬀ, K.; Fluharty, C.; Fluharty, A.; Faull, K. F. J. Lipid Res. 2005, 46, 2254–2264.
Zamek-Gliszczynski, M. J.; Nezasa, K.-I.; Tian, X., Kalvass, J. C.; Patel, N. J.; Raub, T. J.; Brouwer, K. L. R. Molec. Pharmacol. 2006, 70, 2127–2133.
Stawoska, I.; Gaweda, S.; Bielak-Lakomska, M.; Brindell, M.; Lewinski, K.; Laidler, P.; Stochel, G. J. Coord. Chem. 2010, 63, 2472–2487.
Seidman, M.; Link, K. P. J. Am. Chem. Soc. 1950, 72, 4324.
Lederberg, J. J. Bacteriol. 1950, 60, 381–392.
Mead, J. A. R.; Smith, J. N.; Williams, R. T. Biochem. J. 1955, 61, 569–574.
Robinson, D. Biochem. J. 1956, 63, 39–44.
Leaback, D. H.; Walker, P. G. Biochem. J. 1961, 78, 151–156.
Hoppe, H.-G. Mar. Ecol. Prog. Ser. 1983, 11, 299–308.
Manaﬁ, M.; Kneifel, W.; Bascomb, S. Microbiol. Rev. 1991, 55, 335–348.
Kato, N.; Suyama, S.; Shirokane, M.; Kato, M.; Kobayashi, T.; Tsukagoshi, N. Appl. Environ. Microbiol. 2002, 68, 1250–1256.
Colombo, V.; Vieira, A. A. H.; Moraes, G. Braz. J. Microbiol. 2004, 35, 110–116.
James, A. L.; Perry, J. D.; Ford, M.; Armstrong, L.; Gould, F. K. Appl. Environ. Microbiol. 1996, 62, 3868–3870. James, A. L.; Perry, J. D.; Ford, M.; Armstrong, L.; Gould, F. K. J. Appl. Microbiol. 1997, 82, 532–536.
James, A. L.; Perry, J. D.; Chilvers, K.; Robson, I. S.; Armstrong, L.; Orr, K. E. Lett. Appl. Microbiol. 2000, 30, 336–340.
James, A. L.; Chilvers, K. F.; Perry, J. D.; Armstrong, L.; Gould, F. K. Appl. Environ. Microbiol. 2000, 66, 5521–5523.
Zheng, W.; Padia, J.; Urban, D. J.; Jadhav, A.; Goker-Alpan, O.; Simeonov, A.; Goldin, E.; Auld, D.; LaMarca, M. E.; Inglese, J.; Austin, C. P.; Sidransky, E., Proc. Nat. Acad. Sci. USA 2007, 104, 13192–13197.
Plovins, A.; Alvarez, A. M.; Ibanez, M.; Molina, M.; Nombelal, C. Appl. Environ. Microbiol. 1994, 60, 4638–4641. Burton, M. EP 1 436 411 B1 /2005.
Roth, N. G., Roth, N. J. US Patent 7,273,719 B2 /2007.
Freeman, C.; Liska, G.; Ostle, N. J.; Jones, S. E.; Lock, M. A. Plant Soil 1995, 175, 147–152.
Robards, K. J. Chromatog. A 2003, 1000, 657–691.
Sun, J.-P.; Wu, L.; Fedorov, A. A.; Almo, S. C.; Zhang, Z.-Y. J. Biol. Chem. 2003, 278, 33392–33399.
Huang, Z.; Wong, C. F. Biophys. J. 2007, 93, 4141–4150.
Liang, F.; Huang, Z.; Lee, S.-Y.; Liang, J.; Ivanov, M. I.; Alonso, A.; Bliska, J. B.; Lawrence, D. S.; Mustelin, T.; Zhang, Z.-Y. J. Biol. Chem. 2003, 278, 41734–41741.
Hu, X.; Vujanac, M.; Stebbins, C. E. J. Molec. Graph. Model. 2004, 23, 175–187.
Kumar, S.; Zhou, B.; Liang, F.; Wang, W.-Q.; Huang, Z.; Zhang, Z.-Y. Proc. Natl. Acad. Sci. USA 2004, 101, 7943–7948.
Huang, Z.; He, Y.; Zhang, X.; Gunawan, A.; Wu, L.; Zhang, Z.-Y.; Wong, C. F. Chem. Biol. Drug Des. 2010, 76, 85–
Lingwood, C.; Mylvaganam, M.; Minhas, F.; Binnington, B.; Branch, D. R.; Pomes, R. J. Biol. Chem. 2005, 280, 12542–12547.
Elovaara, E.; Mikkola, J.; Luukkanen, L.; Antonio, L.; Fournel-Gigleux, S.; Burchell, B.; Magdalou, J.; Taskinen, J. Drug Metab. Dispos. 2004, 32, 1426–1433.
M¨ annist¨ o, P. T.; Kaakkola, S. Pharmacol. Rev. 1999, 51, 593–628.
Robinson, D.; Smith, J. N.; Williams, R. T. Biochem. J. 1951, 50, 228–235.
Parke, D. V. Biochem. J. 1956, 62, 339–346.
Chrastil, J.; Wilson, T. J. J. Pharmacol. Exp. Ther. 1975, 193, 631–638.
Billings, R. E. Drug Metab. Dispos. 1985, 13, 287–290.
Jain, R. K.; Dreisbach, J. H.; Spain, J. C. Appl. Environm. Microbiol. 1994, 60, 3030–3032.
Zdr´ ahal, Z. J. Chromatogr. 1998, A 793, 214–219.
Iga, D. P.; Iga, S.; Nicolescu, A.; Chira, N.-A. Rev. Roum. Chim. 2010, 55, 357–363.
Lemieux, R. U. Meth. Carbohydr. Chem. 1963, 2, 221–222.
Conchie, J.; Levvy, G. A. Methods Carbohydr. Chem. 1963, 2, 345–347.
Smits, E.; Engberts, J. B. F. N.; Kellogg, R. M.; van Doren, H. A. J. Chem. Soc., Perkin Trans. 1996, 1, 2873–2877. Cepanec, I.; Litvic, M. Arkivoc 2008, (ii), 19–24.
Fletcher, H. G., Jr. Methods Carbohydr. Chem. 1963, 2, 226–228.
D’Accorso, N. B.; Thiel, I. M. E.; Sch¨ uller, M. Carbohydr. Res. 1983, 124, 177–184.
Iga, D. P.; Iga, S.; Schmidt, R. R.; Buzas, M. C. Carbohydr. Res. 2005, 340, 2052–2054.
Li, Y.-T.; Li, S.-C. Methods Enzymol. 1972, 28 (Part B), 702–713.
Li, Y.-T.; Li, S.-C. Methods Enzymol. 1972, 28 (Part B), 714–720.
Agrawal, K. M. L.; Bahl, O. P. Methods Enzymol. 1972, 28 (Part B), 720–728.
Iga, S.; Ion, A.; Mencinicopschi, G.; Iga, D. P. St. Tehnol. Alim. 1994, 2, 2–4.
Iga, D. P.; Portokalakis, P. In Proteins of Seminal Plasma; Shivaji, S.; Scheit, K.-H.; Bhargava, P. M., Eds.; John Wiley & Sons, New York, 1990.
Worwood, M.; Dodgson, K. S.; Hook, G. E. R.; Rose, F. A. Biochem J. 1973, 134, 183–190.
Lowry, O. H.; Rosebrough, N. J.; Farr, A. L.; Randall, R. J. J. Biol. Chem. 1951, 193, 265–275.
Robinson, D.; Smith, J. N.; Williams, R. T. Biochem. J. 1951, 50, 221–227.
Biggins, R.; Haslam, E. J. Chem. Soc. 1965, 6883–6888.
Sue, M.; Ishihara, A.; Iwamura, H. Planta 2000, 210, 432–438.
Howard, S.; He, S.; Withers, S. G. J. Biol. Chem. 1998, 273, 2067–2072.
Kimura, Y.; Hess, D.; Sturm, A. Eur. J. Biochem. 1999, 264, 168–175.
Sekimata, M.; Ogura, K.; Tsumuraya, Y.; Hashimoto, Y.; Yamamoto, S. Plant Physiol. 1989, 90, 567–574.
Manaﬁ, M. Int. J. Food Microbiol. 1996, 31, 45–58.
Bascomb, S., Manaﬁ, M. Clin. Microb. Rev. 1998, 11, 318–340.
Perry, J. D.; Morris, K. A.; James, A. L.; Oliver M.; Gould, F. K. J. Appl. Microbiol. 2007, 102, 410–415.
Van Tilbeurgh, H.; Claeyssens, M.; De Bruyne, C. K. FEBS Lett. 1982, 149, 152–156.
Parry, N. J.; Beever, D. E.; Owen, E.; Vandenberghe, I.; Van Beeumen, J.; Bhat, M. K. Biochem. J. 2001, 353, 117–127.
Chauve, M.; Mathis, H.; Huc, D.; Casanave, D.; Monot, F.; Ferreira, N. L. Biotechnol. Biofuels 2010, 3, 1–8.
Muto, N.; Suga, S.; Fuji, K.; Goto, K.; Yamamoto, I. Agric. Biol. Chem. 1990, 54, 1697–1703.
Kr¨ oger, L.; Thiem, J. Carbohydr. Res. 2007, 342, 467–481.
Johnson, W. G.; Gal, A. E.; Miranda, A. F.; Pentchev, P. G. Clin. Chim. Acta 1980, 102, 91–97.
Barns, R. J.; Clague, A. E. Clin. Chim. Acta 1982, 120, 57–63.
Wiederschain, Ya. G.; Kozlova, I. K.; Ilyina, G. S.; Mikhaylova, M. A.; Beyer E. M. Carbohydr. Res. 1992, 224, 255–272.
Molzer, B.; Sundt-Heller, R.; Kainz-Korschinsky, M.; Zobel, M. Amer. J. Med. Genet. 1992, 44, 523–526.
Schestag, F.; Yaghootfam, A.; Habetha, M.; Poeppel, P.; Dietz, F.; Klein, R. A.; Zlotogora, J.; Gieselmann, V. Biochem. J. 2002, 367, 499–504.
Hoppe, H.-G. In Handbook of Methods in Aquatic Microbial Ecology; Kemp, P. P.; Sherr, B. F.; Sherr, E. B.; Cole, J. J., Eds.; Lewis Publishers, Boca Raton, FL, 1993.
Boschker, H. T. S.; Cappenberg, T. E. Appl. Environ. Microbiol. 1994, 60, 3592–3596.
Martinez, J.; Smith, D. C., Steward, G. F.; Azam, F. Aquat. Microb. Ecol. 1996, 10, 223–230.