From Lactose to Alkyl Galactoside Fatty Acid Esters as Non-Ionic Biosurfactants: A Two-Step Enzymatic Approach to Cheese Whey Valorization.

A library of alkyl galactosides was synthesized to provide the "polar head" of sugar fatty acid esters to be tested as non-ionic surfactants. The enzymatic transglycosylation of lactose resulted in alkyl ß-D-galactopyranosides, whereas the Fischer glycosylation of galactose afforded isomeric mixtures of α- and ß-galactopyranosides and α- and ß-galactofuranosides. n-Butyl galactosides from either routes were enzymatically esterified with palmitic acid, used as the fatty acid "tail" of the surfactant, giving the corresponding n-butyl 6-O-palmitoyl-galactosides. Measurements of interfacial tension and emulsifying properties of n-butyl 6-O-palmitoyl-galactosides revealed that the esters of galactopyranosides are superior to those of galactofuranosides, and that the enantiopure n-butyl 6-O-palmitoyl-ß-D-galactoside, prepared by the fully enzymatic route, leads to the most stable emulsion. These results pave the way to the use of lactose-rich cheese whey as raw material for the obtainment of bio-based surfactants.

2-O-Acetyl-3,4,5,6-tetra-O-benzyl-d-myo-inosityl diphenylphosphate: A new useful intermediate to inositol phosphate and phospholipids.

Inositol phosphates and inositol phospholipids are ubiquitous in biochemistry and play a central role in cell signaling and regulation events. For this reason, their synthesis has attracted widespread interest. This paper describes the preparation of a new optically active inositol phosphate derivative, 2-O-acetyl-3,4,5,6-tetra-O-benzyl-d-myo-inosityl diphenylphosphate (6), and its characterization by spectroscopic methods. Compound (6) represents a useful intermediate for the preparation of inositol phosphate and phospholipids, in particular of glycerophosphoinositol (GPI), a natural anti-inflammatory agent.