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New Class of Glycoside Hydrolase Mechanism-Based Covalent Inhibitors: Glycosylation Transition State Conformations

Journal of the American Chemical Society, 2017
The design of covalent inhibitors in glycoscience research is important for the development of chemical biology probes. Here we report the synthesis of a new carbocyclic mechanism-based covalent inhibitor of an α-glucosidase. The enzyme efficiently catalyzes its alkylation via either an allylic cation or a cationic transition state.
Saeideh Shamsi Kazem Abadi   +5 more
openaire   +2 more sources

Recent advances in glycoside hydrolase family 20 and 84 inhibitors: Structures, inhibitory mechanisms and biological activities

Bioorganic Chemistry
Glycoside hydrolase family 20 (GH20) β-N-acetyl-d-hexosaminidase (Hex) catalyzes the cleavage of glycosidic linkages in glycans, glycolipids and glycoproteins, and is involved in glycoprotein modification, metabolism of glycoconjugate and the degradation of chitin in fungal cell walls and arthropod exoskeletons. GH84 O-β-N-acetyl-d-glucosaminidase (OGA)
Xi Jiang
exaly   +3 more sources

Glycoside Hydrolases: Mechanistic Information from Studies with Reversible and Irreversible Inhibitors

1990
Publisher Summary This chapter discusses the results of the studies that permit some generalizations on the catalytic mechanism of glycoside hydrolases from widely differing sources and with different sugar and aglycon specificities and that have become available over the past 15 years.
openaire   +2 more sources

The synthesis of a carbohydrate-like dihydrooxazine and tetrahydrooxazine as putative inhibitors of glycoside hydrolases: A direct synthesis of isofagomine

Canadian Journal of Chemistry, 2002
The treatment of benzyl 2,3-O-isopropylidene-β-L-xylopyranoside with N-hydroxyphthalimide under Mitsunobu conditions, followed by protecting-group interchange, gave benzyl 4-O-[(tert-butoxycarbonyl)amino]-2,3- O-isopropylidene-α-D-arabinoside. Mild acid hydrolysis and catalytic hydrogenolysis afforded 4-O-[(tert-butoxycarbonyl)amino]-D-arabinose that,
Wayne M Best   +5 more
openaire   +1 more source

Discovery of glycosidated glycyrrhetinic acid derivatives: Natural product-based soluble epoxide hydrolase inhibitors

European Journal of Medicinal Chemistry
There are few reports on soluble epoxide hydrolase (sEH) structure-activity relationship studies using natural product-based scaffolds. In this study, we discovered that C-30 urea derivatives of glycyrrhetinic acid such as 33, rather than C-20/C-3 urea derivatives, possess in vitro sEH inhibitory capabilities.
Qian Liu   +12 more
openaire   +2 more sources

ChemInform Abstract: The Synthesis of Some Epoxyalkyl β‐C‐Glycosides as Potential Inhibitors of β‐Glucan Hydrolases.

ChemInform, 1997
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
W. M. BEST   +4 more
openaire   +1 more source

ChemInform Abstract: Cyclic Guanidinium Ions as Analogues of Glycosyl Cations are Competitive and Noncompetitive Inhibitors of Glycoside Hydrolases.

ChemInform, 1995
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
J. LEHMANN, B. ROB
openaire   +1 more source

ChemInform Abstract: Glycoside Hydrolases: Mechanistic Information from Studies with Reversible and Irreversible Inhibitors

ChemInform, 1991
AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
openaire   +1 more source

Discovery of a Novel Microbial Glycoside Hydrolase Directing Formation of New α‐Amylase Inhibitors

Chemistry – A European Journal
ABSTRACT Glycoside hydrolases (GHs) comprise a large and diverse family of enzymes that catalyze the hydrolysis of glycosidic bonds in a wide range of glycan substrates, including polysaccharides, oligosaccharides, and glycoconjugates.
Tong Zou   +4 more
openaire   +1 more source

Treatment of non-insulin dependent diabetic adults with a new glycoside hydrolase inhibitor (Bay g 5421).

Arzneimittel-Forschung, 1981
The hypoglycemic effect of a glycoside hydrolase inhibitor (BAY g 5421) was tested in 10 non-insulin dependent, overweight diabetics by means of continuous in vivo glucograms. There was a highly significant reduction of serum glucose with a dosage of 3 x 100 mg glycoside hydrolase inhibitor, after dosage division to 6 x 50 mg there was an additional ...
D, Sailer, G, Röder
openaire   +1 more source

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