Glycolipids synthesis: improved hydrazinolysis conditions for preparation of 1, 2-polyunsaturated fatty acyl-β-monogalactosyl-glycerols. (7th April 2016)

• Record Type: Journal Article
• Authors: Pagano, Dario; Cutignano, Adele; Manzo, Emiliano; Tinto, Francesco; Fontana, Angelo
• Is Part Of: Carbohydrate research. Volume 424(2016)
• Page Start: 21
• Page End: 23
• Publication Date: 2016-04-07
• Subjects: Galactolipids -- Bioactive lipids -- Protecting group -- Acetate -- Synthetic method -- Organic synthesis; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2016.02.005
• Languages: English
• ISSNs: 0008-6215

Abstract

Highlights: A series of 1, 2- O -diacyl-3- O -(β-2', 3', 4', 6'-tetra-acetyl-galactopyranosyl)-glycerol analogs with fatty acids from palmitoleic to arachidonic were synthetized according to published procedure. Application of the usual hydrazinolysis experimental conditions to the synthetic 1, 2- O -diacyl-3- O -[(2', 3', 4', 6'-tetra-acetyl)-β-D-galactosyl]-glycerols analogs gave partially hydrogenated by-products. Exceptionally mild and selective removal of acetate protecting groups by improved conditions of hydrazinolysis has been developed and applied for a safer strategy for synthesis of poly-unsaturated fatty acyl β-glycolipids. Graphical abstract: Abstract: The investigation is related to the development of a general strategy for the synthesis of glycolipids including analogs bearing polyunsaturated fatty acids. In particular, here we report exceptionally mild and selective conditions to remove acetate protecting groups from glyceroglycolipids by hydrazinolysis. Synthetic 1, 2- O -di-arachidonoyl-3- O -β-galactosyl-glycerol was used as representative of polyunsaturated β-galactosyl-di-acyl-glycerols due to its reactivity under the conditions usually employed in literature.