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 |
References
- 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).
- Hunger, K. Industrial Dyes: Chemistry, Properties, Applications. , 1st, Weinheim. Wiley-VHC. (2003).
- Kiernan, J. A. Indigogenic Substrates for Detection and Localization of Enzymes. Biotechn. Histochem. 82, 73-103 (2007).
- Barnett, R. J., Seligman, A. M. Histochemical Demonstration of Esterases by Production of Indigo. Science. 114, 579-582 (1951).
- 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).
- Anderson, F. B., Leaback, D. H. Substrates for the Histochemical Localization of some Glycosidases. Tetrahedron. 12, 236-239 (1961).
- 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).
- 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).
- 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).
- 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).
- 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).
- 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).
- Marmuse, L., et al. New Chromogenic Substrates for Feruloyl Esterases. Org. Biomol. Chem. 6, 1208-1214 (2008).
- 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).
- Robertson, A. J. Syntheses of Glucosides. Part I. The Synthesis of Indican. Chem. Soc. , 1937-1943 (1927).
- Robertson, A., Waters, R. B. J. Synthese of Glucosides. Part VII. The Synthesis of 6-Bromoindican. Chem. Soc. , 2239-2243 (1929).
- Böttcher, S., Thiem, J. Indoxylic Acid Esters as Convenient Intermediates Towards Indoxyl Glycosides. Eur. J. Org. Chem. , 564-574 (2014).
- 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).
- Böttcher, S., Thiem, J. Facile Preparation of Indoxyl- and Nitrophenyl Glycosides of Lactosamine and Isolactosamine. RSC Adv. 4, 10856-10861 (2014).