95066-28-7Relevant articles and documents
Synthesis and inhibition properties of a series of pyranose derivatives towards a Zn-metalloproteinase from Saccharomonospora canescens
Dolashka-Angelova, Pavlina,Abdel-Jalil, Raid J.,Al-Qawasmeh, Raed A.,Stambolieva, Nicolina,Voelter, Wolfgang
experimental part, p. 2343 - 2347 (2010/11/18)
The Zn-proteinase, isolated from Saccharomonospora canescens (NPS), shares many common features with thermolysin, but considerable differences are also evident, as far as the substrate recognition site is concerned. In substrates of general structure AcylAlaAlaPhe 4NA, this neutral proteinase cleaves only the arylamide bond (non-typical activity of Zn-proteinases), while thermolysin attacks the peptide bond Ala-Phe. Phosphoramidon is a powerful tight binding inhibitor for thermolysin and significantly less specific towards NPS. The Ki-values (65 μM for NPS vs 0.034 μM for thermolysin) differ nearly 2000-folds. This implies significant differences in the specificity of the corresponding subsites. The carbohydrate moiety is supposed to accommodate in the S1-subsite and the series of arabinopyranosides and glucopyranosides (12 compounds), which are assayed as inhibitors in a model system: NPS with SucAlaAlaPhe4NA as a substrate could be considered as mapping the S1-subsite of NPS. Members of the series with an additional ring (3,4-epithio, 3,4-anhydro-derivatives) turned out to be reasonably good competitive inhibitors (Ki ≈ 0.1-0.2 mM are of the same order as the Ki value for phosphoramidon). The structure of these compounds (8, 9, 11 and 12) seems to fit the size of the S1-subsite and due to an appropriately oriented OH-group in addition, to protect the active site Zn2+.
Regioselective and Stereoselective Oxirane Ring-Openings of 2,3-Anhydropentopyranosides with Some Methyl Group Donating Organometallic Reagents
Inghardt, Tord,Frejd, Torbjoern,Magnusson, Goeran
, p. 4542 - 4548 (2007/10/02)
By the proper choice of methyl group transferring reagents organometallic (Me4AlLi, Me4AlLi/MeLi (1:1), Me2CuLi, Me3Al, Me2Mg) it is possible to selectively introduce a methyl group into the 2- or 3-position via epoxide ring-opening of four easily availab
Novel One-Pot Synthesis of a New Class of Compounds Involving Coupling of Sugars and Amino Acids via Triflates.
Kowollik, W.,Malik, A.,Afza, N.,Voelter, W.
, p. 3325 - 3330 (2007/10/02)
A new class of pharmacologically interesting compounds has been synthesized by way of a novel C-N coupling reaction between partially blocked sugars and a variety of suitably protected naturally occuring amino acids.The free amino functions of the latter