Abstract
吲哚酚甙被证明是监测糖苷酶活动的宝贵和灵活的工具。 Indoxyls通过酶水解释放，并迅速被氧化，例如通过大气中的氧，靛蓝类染料。这个反应能够快速和容易的掩护体内不分离或酶的纯化，以及在琼脂平板上或在溶液中快速检测（ 例如，蓝白斑筛选，微井）和用于生物化学，组织化学，细菌学和分子生物学。不幸的是这样的基片的合成被证明是困难的，由于各种副反应和吲哚酚羟基官能的反应性低。特别是对于葡萄糖型结构低收益率的变化。我们的新方法使用indoxylic酸酯作为关键中间体。 Indoxylic酸酯具有不同的图案取代了可伸缩的途径准备。这些受体和乙酰化相转移糖基化糖基卤化物可以高收率常见的条件下进行。酯裂解和随后的温和银介导的糖基化得到高收率的过酰化吲哚酚苷。最后的脱保护是根据普伦执行。
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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