Publication

Synthesis of (+)-3,7,8-trideoxy-3,7-imino-D-threo-L-galacto-octitol and its inhibition of beta-glucosidases

Pierre Vogel
1996
Journal Articles

Abstract

The readily available 2,3:6,7-di-O-isopropylidene-D-glycero-D-gulo-heptono-1,4-lactone [(-)-5] was converted in four synthetic steps into the new iminooctitol (+)-3,7,8-trideoxy-3,7-imino-D-threo-L-galacto-octitol [(+)-10]. Although the piperidine unit of (+)-10 has the absolute configuration of beta-D-galacto-hexopyranosides, this iminoalditol does not inhibit five commercially available beta-galactosidases. However, (+)-10 was found to be a good competitive inhibitor of beta-glucosidases from almond (K-i = 15 mu M) and from Caldocellum saccharolyticum (K-i = 41 mu M).

Official source

https://infoscience.epfl.ch/entities/publication/67c142bc-fd91-4995-a9e4-99dd95bffcd4

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Pierre Vogel
1996
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/67c142bc-fd91-4995-a9e4-99dd95bffcd4

About this result

Related concepts (3)

Competitive inhibition

Competitive inhibition is interruption of a chemical pathway owing to one chemical substance inhibiting the effect of another by competing with it for binding or bonding. Any metabolic or chemical messenger system can potentially be affected by this principle, but several classes of competitive inhibition are especially important in biochemistry and medicine, including the competitive form of enzyme inhibition, the competitive form of receptor antagonism, the competitive form of antimetabolite activity, and the competitive form of poisoning (which can include any of the aforementioned types).

Enzyme inhibitor

An enzyme inhibitor is a molecule that binds to an enzyme and blocks its activity. Enzymes are proteins that speed up chemical reactions necessary for life, in which substrate molecules are converted into products. An enzyme facilitates a specific chemical reaction by binding the substrate to its active site, a specialized area on the enzyme that accelerates the most difficult step of the reaction.

Receptor antagonist

A receptor antagonist is a type of receptor ligand or drug that blocks or dampens a biological response by binding to and blocking a receptor rather than activating it like an agonist. Antagonist drugs interfere in the natural operation of receptor proteins. They are sometimes called blockers; examples include alpha blockers, beta blockers, and calcium channel blockers. In pharmacology, antagonists have affinity but no efficacy for their cognate receptors, and binding will disrupt the interaction and inhibit the function of an agonist or inverse agonist at receptors.