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Synthesis of glycosylated aminothiol from D-glucose as promising anti-tubercular agent

Authors : Archana Singh a, Virendra Prasad a, Sanchayita Rajkhowa b, Vishwa D. Tripathi c and Vinod K. Tiwari *a


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Abstract

A facile method for a series of novel glycosylated -aminothiols by employing TBAB/NEt3-catalyzed ring opening of thiirane ring of D-glucose-derived 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene--D-glucofuranose with different primary and secondary amines including aliphatic, aromatic, heterocyclic, and glycosyl amine has been devised. Diamines on the other hand for thiirane ring opening of anhydroglucose derivative led to the formation of respective bis-glycosylated N1,Nn-diaminothiols in good yield. The method is straight forward, economical, high-yielding and easy to scale up. One of the glycosylated aminothiol contains both the hydrophilic carbohydrate moiety and hydrophobic hexadecyl residue, thus can serve a promising candidate to exhibit surface-active properties. The resulted glycosylated -aminothiols may serve as an interesting scaffold to develop mechanism- based novel chemotherapeutic agents.

Keyword

Glycosyl thiirane, oxirane, glycosyl aminothiol, diaminothiols, tuberculosis, surfactant