Determination of protonation states of iminosugar–enzyme complexes using photoinduced electron transfer† †Electronic supplementary information (ESI) available: NMR spectra of new compounds, experimental details and Fig. S1–S5 (19 pages). See DOI: 10.1039/c7sc01540b Click here for additional data file.
نویسندگان
چکیده
A series of N-alkylated analogues of 1-deoxynojirimycin containing a fluorescent 10-chloro-9-anthracene group in the N-alkyl substituent were prepared. The anthracene group acted as a reporting group for protonation at the nitrogen in the iminosugar because an unprotonated amine was found to quench fluorescence by photoinduced electron transfer. The new compounds were found to inhibit bglucosidase from Phanerochaete chrysosporium and a-glucosidase from Aspergillus niger, with Ki values in the low microto nanomolar range. Fluorescence and inhibition versus pH studies of the bglucosidase–iminosugar complexes revealed that the amino group in the inhibitor is unprotonated when bound, while one of the active site carboxylates is protonated.
منابع مشابه
Very bright mechanoluminescence and remarkable mechanochromism using a tetraphenylethene derivative with aggregation-induced emission† †Electronic supplementary information (ESI) available: Details of the synthesis; structural information for the compound (NMR, IR, and mass spectra); Tables S1–S5; Fig. S1–S11. CCDC 1037840 and 1057432. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc00466g Click here for additional data file. Click here for additional data file. Click here for additional data file. Click here for additional data file.
PCFM Lab, GD HPPC Lab, Guangdong Eng High-performance Organic and Polymer P Laboratory of Opto-electronic Material and Chemical Engineering, Sun Yet-sen Univers [email protected]; [email protected] 20 84112222; Tel: +86 20 84112712 State Key Laboratory of Optoelectronic Mat and Engineering, Sun Yat-sen University, Gu Shenzhen China Star Optoelectronics Techn TCL Corporate Research, Guangdon...
متن کاملFacile synthesis of oligoyne amphiphiles and their rotaxanes† †Electronic supplementary information (ESI) available: Fig. S1–S4 and a comprehensive account of all experimental details, including synthetic procedures, analytical data, and NMR spectra of all novel compounds. See DOI: 10.1039/c4sc03154g Click here for additional data file.
متن کامل
Homochiral self-assembly of biocoordination polymers: anion-triggered helicity and absolute configuration inversion† †Electronic supplementary information (ESI) available: Preparation and physical characterization data of 1P and 2M, additional structural description, UV-Vis and CD spectra (Fig. S1–S7), crystallographic refinement details for 1P and 2M (Table S1), selected bond distances and angles for 1P and 2M (Tables S2–S5), ESI(+)-MS and ESI(+)-MSMS spectra (Fig. S8–S11 and Schemes S1 and S2) and PXRD (Fig. S12). CCDC 1046609 and 1046610. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc01089f Click here for additional data file. Click here for additional data file.
متن کامل
Mechanisms and applications of cyclometalated Pt(ii) complexes in photoredox catalytic trifluoromethylation† †Electronic supplementary information (ESI) available: Experimental details and the syntheses of the Pt(ii) catalysts; Fig. S1–S55, showing the phosphorescence spectra, femto- and nanosecond laser flash photolysis results, cyclic and differential pulse voltammograms, phosphorescence quenching experiment results, photoinduced ESR spectrum, spectroelectrochemical UV-vis-NIR absorption spectrum, dark-state reaction results, and 1H, 13C, and 19F NMR spectra; Scheme S1, presenting the synthetic routes to the Pt(ii) complexes; Tables S1–S6, listing optimization results for the trifluoromethylation of 1-dodecene, 3-methylindole and N-methylpyrrole, and the Cartesian coordinates for the optimized geometries of one-electron oxidized species of the Pt complexes. See DOI: 10.1039/c4sc02537g Click here for additional data file.
Department of Advanced Materials Engin Kyung Hee University, Yongin, Gyeonggi-do 4 Department of Applied Chemistry & Depa University, Ansan, Gyeonggi-do 426-791, Ko Department of Material and Life Science, University, ALCA, Japan Science and Tech 0871, Japan. E-mail: [email protected] † Electronic supplementary information ( the syntheses of the Pt(II) catalysts; Fig. spectra, femtoand nanose...
متن کامل