Peculiar behavior of starch 2, 3-dialdehyde towards sulfanilamide and sulfathiazole. (5th November 2016)

• Record Type: Journal Article
• Authors: Keshk, Sherif M.A.S.; Ramadan, Ahmed M.; Al-Sehemi, Abdullah G.; Yousef, El Sayed; Bondock, Samir
• Is Part Of: Carbohydrate polymers. Volume 152(2016)
• Page Start: 624
• Page End: 631
• Publication Date: 2016-11-05
• Subjects: Dialdehyde starch -- Periodate oxidation -- Aldehyde content -- Schiff's bases -- Sulfa drugs; Polysaccharides -- Periodicals; Polysaccharides -- Periodicals; Polysaccharides -- Périodiques; Electronic journals; 547.78
• DOI: 10.1016/j.carbpol.2016.07.061
• Languages: English
• ISSNs: 0144-8617

Abstract

Highlights: Synthesis of two novel Schiff's base. Difference in reactivity aldehyde starch and aldehyde cellulose towards Schiff base formation. Starch aldehyde reactivity comparison towards sulfanilamide and sulfathiazole. Abstract: In this study, starch (1 ) was oxidized to starch-2, 3-dialdehyde (DAS;2 ) using potassium periodate. In addition, two novel Schiff's bases (5 &6 ) were synthesized via a condensation reaction between DAS (2 ) and sulfa drugs (sulfanilamide;3 & sulfathiazole;4 ). The synthesized Schiff's bases (5 &6 ) were characterized by FT-IR spectroscopy, X-ray diffraction and DSC analysis. DAS can easily be oxidized owing to its high aldehyde content (91.0%). However, it has low reactivity towards sulfanilamide (3 ) and sulfathiazole (4). According to the diffraction functional theory, this peculiar behavior is caused by the absence of V-shape in α−glucan linkage in DAS molecules, making the carbonyl group least electropositive. This reduces the nucleophilic attacks of the amino group in sulfa drugs towards the carbonyl group in DAS.