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Purin-6-yl 6-deoxy-1-thio-β-d-glucopyranoside. Enzymology, chemistry, and cytotoxicity

✍ Scribed by Charles K. Zercher; Leo R. Fedor

Publisher: Elsevier Science
Year: 1987
Tongue: English
Weight: 545 KB
Volume: 165
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(87)80106-4

No coin nor oath required. For personal study only.

✦ Synopsis

Pm-in-6-yl 6-deoxy-1-thio-P-o-glucopyranoside ( 4) is a substrate for almond /I-glucosidase and a weak competitive inhibitor of bovine liver P-D-glucuronidase (Ki -20mM). Both 4 and purine-protonated 4 undergo hydrolysis catalyzed by dilute acid in the pH range 0.17-2.59. These results are compared with those previously obtained with ammonium (purind-yl 1-thio-Po-glucopyranosid)uronate, (purind-yl 1-thio-P-D-glucopyranosid)uronamide, purind-yl l-thio-P-D-glucopyranoside, and purin-6-yl2-deoxy-1-thio-p-D-glucopyranoside, and it is concluded that the data support an involvement of substituents at C-5 in producing productive Michaelis-complex conformers. The 6-deoxyglucoside is more active than the D-glucosiduronic acid in an L1210 mouse screen.

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