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Family of thiomercuric derivatives of sugars: Synthesis, fungicidal/herbicidal activity, and application to the X‐ray structure determination of the corresponding enzymes
Author(s) -
Belakhov Valery,
Dor Evgenia,
Hershenhorn Joseph,
Botoshansky Mark,
Bravman Tsafrir,
Kolog Mirit,
Shoham Yuval,
Shoham Gil,
Baasov Timor
Publication year - 2001
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1560/e8dm-02pk-dl0v-u7fr
Subject(s) - chemistry , orthorhombic crystal system , enzyme , anomer , stereochemistry , covalent bond , molecule , x ray , crystallography , crystal structure , organic chemistry , physics , quantum mechanics
Abstract 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 K i 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)‐ß‐D‐xyloside ( 3 ) affords crystals belonging to the orthorhombic space group P 2 1 2 1 2 1 and at 293(2) K: a = 6.7510(2), b = 9.7140(2), c = 29.4770(9) Å, V = 1933.08(9) Å, Z = 8, R ( F 2 ) = 0.0329, and R w ( F 2 ) = 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.