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.
Modular Synthesis of Aryl Thio/Selenoglycosides via the Catellani Strategy
Ding, Ya-Nan,Huang, Yan-Chong,Shi, Wei-Yu,Zheng, Nian,Wang, Cui-Tian,Chen, Xi,An, Yang,Zhang, Zhe,Liang, Yong-Min
supporting information, p. 5641 - 5646 (2021/08/01)
We described a novel palladium-catalyzed domino procedure for the preparation of (hetero)aryl thio/selenoglycosides. Readily available (hetero)aryl iodides and easily accessible 1-thiosugars/1-selenosugars are utilized as the substrates. Meanwhile, 10 types of sugars are quite compatible with this reaction with good regio- and stereoselectivity, high efficiency, and broad applicability (up to 89%, 53 examples). This method enables the straightforward formation of the C(sp2)-S/Se bond of (hetero)aryl thio/selenoglycosides.
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.