6739-54-4Relevant articles and documents
Family of thiomercuric derivatives of sugars: Synthesis, fungicidal/herbicidal activity, and application to the x-ray structure determination of the corresponding enzymes
Belakhov, Valery,Dor, Evgenia,Hershenhorn, Joseph,Botoshansky, Mark,Bravman, Tsafrir,Kolog, Mirit,Shoham, Yuval,Shoham, Gil,Baasov, Timor
, p. 177 - 188 (2000)
A series of thiomercuric derivatives of mono-and disaccharides 1-7, in which methylmercury or phenylmercury is covalently attached to anomeric thioglycosides, were synthesized for structure-function studies of glycosidases. Thiomethylmercuryl xylobiosides 5 and 6 were found to inhibit intracellular xylanase-T6 in a competitive manner, with Ki values of 0.35 mM and 0.01 mM, respectively. These inhibitors have been co-crystallized with the enzyme and are being used for X-ray analysis. 1-(Thiomethylmercuric)-β-D-xyloside (3) affords crystals belonging to the orthorhombic space group P212121 and at 293(2) K: a = 6.7510(2), b = 9.7140(2), c = 29.4770(9) A, V = 1933.08(9) A, Z = 8, R(F2) = 0.0329, and R (F2) = 0.0626. There are two molecules (A and B) in the asymmetric unit, and each one shows an almost linear S-Hg-C arrangement. Biological tests on 1-7 indicated that they exhibit potent fungicidal and herbicidal activities.
Improved Synthesis of 1-Glycosyl Thioacetates and Its Application in the Synthesis of Thioglucoside Gliflozin Analogues
Dong, Hai,Feng, Guang-Jing,Luo, tao,Lv, Jian,Wang, Shuang-Shuang,Wu, Yuzhou
, p. 2940 - 2949 (2021/07/26)
An improved method to synthesize 1-glycosyl thioacetates was developed, where per-O-acetylated glycoses were allowed to directly react with potassium thioacetate (KSAc) in the presence of BF3 ? Et2O in ethyl acetate under mild conditions. This method not only overcomes the disadvantage of the traditional one-step method, which is that the odorous and toxic thioacetic acid has to be used, but also overcomes the disadvantage of the traditional two-step method, which is that the unstable intermediate, glycosyl halide, has to be synthesized from the per-O-acetylated glycose in advance. Based on this, the per-O-acetylated glucosyl disulfide and the per-O-acetylated glucosyl 1-thiol were efficiently synthesized in high yields (91 % and 90 % respectively) starting from per-O-acetylated glycoses in two-step without the need to isolate intermediate products. Through metal-catalyzed cross-coupling of per-O-acetylated glucosyl 1-thiol with aryl-iodide under very mild conditions, two thioglucoside gliflozin analogues were efficiently synthesized in high yields for the first time. These two thioglucoside gliflozin analogues were further confirmed to be stable to hydrolysis of β-glucosidase.
Selective S-deacetylation inspired by native chemical ligation: practical syntheses of glycosyl thiols and drug mercapto-analogues
Shu, Penghua,Zeng, Jing,Tao, Jinyi,Zhao, Yueqi,Yao, Guangmin,Wan, Qian
supporting information, p. 2545 - 2551 (2015/04/22)
Glycosyl thiols are useful building blocks for the construction of compounds of biological and synthetic importance. Herein, we report a practical synthetic approach toward the efficient synthesis of glycosyl thiols via chemo- and regioselective S-deacetylation inspired by native chemical ligation. This strategy allows the large scale synthesis of glycosyl thiols by simple purification steps without column chromatography. In addition, deacetylation reagents (DTT) could also be recovered and regenerated by a simple process. Thiol containing taxol and artemisinin analogues were successfully prepared based on this methodology. Finally, auranofin, a glucose-based oral drug used to treat rheumatoid arthritis, was synthesized in concise steps and overall high yields.
