Publication

Synthesis of N-substituted (3S,4S)- and (3R,4R)-pyrrolidine-3,4-diols: Search for new glycosidase inhibitors

Pierre Vogel
2004
Journal Articles

Abstract

N-Substituted (3S,4S)- and (3R,4R)-pyrrolidine-3,4-diols 9 and 10, respectively, were derived from (+)-L- and (-)-D-tartaric acid, respectively. Compounds 9k, 91, and 9m with the N-substituents, BnNH(CH2)(2), 4-Phc(6)H(4)CH(2)NH(CH2)(2) and 4-ClC6H4CH2NH(CH2)(2), respectively, showed modest inhibitory activities toward aD-amyloglucosidases from Aspergillus niger and from Rhizopus mold (Table 1). Unexpectedly, several (3R,4R)-pyrrolidine-3,4-diols 10 showed inhibitory activities toward alpha-D-mannosidases from almonds and from jack bean (Table 3). N-Substitution by the NH2(CH2)(2) group, i.e., 10g, led to the highest potency.

Official source

https://infoscience.epfl.ch/entities/publication/1b65177d-9566-4c06-9999-c44a6958cc63

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Pierre Vogel
2004
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/1b65177d-9566-4c06-9999-c44a6958cc63

About this result

Related concepts (17)

Substitution reaction

A substitution reaction (also known as single displacement reaction or single substitution reaction) is a chemical reaction during which one functional group in a chemical compound is replaced by another functional group. Substitution reactions are of prime importance in organic chemistry. Substitution reactions in organic chemistry are classified either as electrophilic or nucleophilic depending upon the reagent involved, whether a reactive intermediate involved in the reaction is a carbocation, a carbanion or a free radical, and whether the substrate is aliphatic or aromatic.

Acid

An acid is a molecule or ion capable of either donating a proton (i.e. hydrogen ion, H+), known as a Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis acid. The first category of acids are the proton donors, or Brønsted–Lowry acids. In the special case of aqueous solutions, proton donors form the hydronium ion H3O+ and are known as Arrhenius acids. Brønsted and Lowry generalized the Arrhenius theory to include non-aqueous solvents.

Tartaric acid

Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes, but also in bananas, tamarinds, and citrus. Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of fermentation. It is commonly mixed with sodium bicarbonate and is sold as baking powder used as a leavening agent in food preparation. The acid itself is added to foods as an antioxidant E334 and to impart its distinctive sour taste.