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Chemistry

Sintesi di indoxyl-glicosidi per il rilevamento di glicosidasi Attività

Published: May 27, 2015 doi: 10.3791/52442

Materials

Name Company Catalog Number Comments
Acetic anhydride Grüssing 10298 Corrosive, flammable
Acetonitrile Sigma-Aldrich 608-001-00-3 Harmful, flammable
Allyl alcohol Aldrich 453021 Harmful, dangerous for the environment
Amberlite IR-120 H+ Fluka 06428 Irritant
Bromoacetic acid Merck 802260 Corrosive, toxic, dangerous for the environment
4-Bromo-3-chloro-2-methylaniline ABCR AB 171687 Irritant
Dichloromethane ACROS 326850010 Harmful
Diethyl ether Grüssing 10274 Harmful, extremly flammable
Dimethylformamide ACROS 348430010 Harmful, flammable
Dimethylsulfoxide Sigma-Aldrich 41648
Ethyl acetate Sigma-Aldrich 607-022-00-5 Irritant, flammable
Ethylenediaminetetraacetic acid AppliChem A1103.0500 Irritant
β1,3-Galactosidase, recombinant, E. coli Calbiochem 345795
Hydrochloric acid VWR 20252.290 Corrosive
Magnesium sulfate hydrate Merck 105885
Methanol ACROS 326950010 Toxic, flammable
Morpholine Janssen Chimica 15.868.57 Corrosive, flammable
Peroleum ether Azelis 111053 Flammable, irritant, dangerous for the environment
Potassium carbonate Grüssing 12005 Corrosive
Potassium permanganate Grüssing 12056 Harmful, oxidising
Potassium tert-butoxide Merck 804918 Corrosive, flammable
Pyridine Sigma-Aldrich 613-002-00-7 Harmful, flammable
Silver acetate Fluka 85140 Irritant, dangerous for the environment
Sodium bicarbonate Grüssing 12144 Corrosive
Sodium hydride Merck 814552 Corrosive, flammable
Sodium hydroxide Riedel-de Häen S181200 Corrosive
Sodium methanolate Merck 806538 Corrosive, flammable
Sodium sulfate Grüssing 12175
Tetrabutylammonium hydrogensulfate Lancaster 5438 Harmful
Tetrahydrofurane Sigma-Aldrich 87371 Harmful, flammable
Tetrakis (triphenylphosphine)palladium(0) Sigma-Aldrich 216666
Triphosgene Fluka 15217 Toxic
Tris (hydroxymethyl)aminomethane hydrochloride Sigma T-3253 Irritant

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References

  1. Clark, R. J. H., Cooksey, C. J., Daniels, M. A. M., Withnall, R. Indigo, Woad, and Tyrian Purple: Important Vat Dyes from Antique to the Present. Endeavour. 17, 191-199 (1993).
  2. Hunger, K. Industrial Dyes: Chemistry, Properties, Applications. , 1st, Weinheim. Wiley-VHC. (2003).
  3. Kiernan, J. A. Indigogenic Substrates for Detection and Localization of Enzymes. Biotechn. Histochem. 82, 73-103 (2007).
  4. Barnett, R. J., Seligman, A. M. Histochemical Demonstration of Esterases by Production of Indigo. Science. 114, 579-582 (1951).
  5. Pearson, B., Andrews, M., Grose, F. Histochemical Demonstration of Mammalian Glucosidase by Means of 3-(5-Bromoindolyl)-β-ᴅ-glucopyranoside. Exp. Biol. Med. 108, 619-623 (1961).
  6. Anderson, F. B., Leaback, D. H. Substrates for the Histochemical Localization of some Glycosidases. Tetrahedron. 12, 236-239 (1961).
  7. Van Dort, M. E., Lee, K. C., Hamilton, C. A., Rehemtulla, A., Ross, B. R. Radiosynthesis and Evaluation of 5-[125I]Iodoindolyl-3-yl-β-ᴅ-galactopyranoside ([125I]IBDG) as a β-Galactosidase Imaging Radioligand. Mol. Imaging. 7, 187-197 (2008).
  8. Yoshida, K., Iino, N., Koga, I. Syntheses of Halogen Substituted β-ᴅ-Glucuronides and Their Hydrolysis by Rabbit Liver β-Glucoronidase. Chem. Pharm. Bull. 32, 1759-1769 (1975).
  9. Horwitz, J. P., et al. Substrates for Cytochemical Demonstartion of Enzyme Activity I. Some Substituted 3-Indolyl-β-ᴅ-glycopyranosides. J. Med. Chem. 7, 574-575 (1964).
  10. Eschenfelder, V., Brossmer, R. 5-Bromo-indol-3-yl 5-Acetamido-3,5-dideoxy-α-ᴅ-glycero-ᴅ-galactononulopyranosidic Acid, a Novel Chromogenic Substrate for the Staining of Sialidase Activity. Glycoconjugate J. 4, 171-178 (1987).
  11. Fujii, I., Iwabuchi, Y., Teshima, T., Shiba, T., Kikuchi, M. X-Neu5Ac: A Novel Substrate for Chromogenic Assay of Neuraminidase Activity in Bacterial Expression Systems. Bioorg. Med. Chem. 1, 147-149 (1993).
  12. Berlin, W., Sauer, B. In situ Color Detection of α-ʟ-Arabinofuranisodase, a "No-Background" Reporter Gene, with 5-Bromo-3-indolyl-α-ʟ-arabinofuranoside. Anal. Biochem. 243, 171-175 (1996).
  13. Marmuse, L., et al. New Chromogenic Substrates for Feruloyl Esterases. Org. Biomol. Chem. 6, 1208-1214 (2008).
  14. Kaneko, S., Kiaoka, M., Kuno, A., Hayashi, K. Syntheses of 4-Methylumbelliferyl-β-ᴅ-Xylobioside and 5-Bromo-3-Indolyl-β-ᴅ-Xylobioside for Sensitive Detection of Xylanase Activity on Agar Plates. Biosci. Biotechnol. Biochem. 64, 741-745 (2000).
  15. Robertson, A. J. Syntheses of Glucosides. Part I. The Synthesis of Indican. Chem. Soc. , 1937-1943 (1927).
  16. Robertson, A., Waters, R. B. J. Synthese of Glucosides. Part VII. The Synthesis of 6-Bromoindican. Chem. Soc. , 2239-2243 (1929).
  17. Böttcher, S., Thiem, J. Indoxylic Acid Esters as Convenient Intermediates Towards Indoxyl Glycosides. Eur. J. Org. Chem. , 564-574 (2014).
  18. Böttcher, S., Hederos, M., Champion, E., Dékány, G., Thiem, J. Novel Efficient Routes to Indoxyl Glycosides for Monitoring Glycosidase Activities. Org. Lett. 15, 3766-3769 (2013).
  19. Böttcher, S., Thiem, J. Facile Preparation of Indoxyl- and Nitrophenyl Glycosides of Lactosamine and Isolactosamine. RSC Adv. 4, 10856-10861 (2014).
Sintesi di indoxyl-glicosidi per il rilevamento di glicosidasi Attività
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Cite this Article

Böttcher, S., Thiem, J.More

Böttcher, S., Thiem, J. Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities. J. Vis. Exp. (99), e52442, doi:10.3791/52442 (2015).

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