Enhanced Synthesis of Alkyl Galactopyranoside by <i>Thermotoga naphthophila</i> β‑Galactosidase Catalyzed Transglycosylation: Kinetic Insight of a Functionalized Ionic Liquid-Mediated System

Green synthesis is of pivotal importance for environmental sustainability. This work reports a novel approach to synthesize an array of alkyl galactopyranosides using thermophilic β-galactosidase from <i>Thermotoga naphthophila</i> RKU-10 (TN1577) as biocatalyst and milk processing waste lactose as galactosyl donor. Ammoeng 102 (only 2.5% addition of total reaction volume), a functionalized ionic liquid (IL) containing tetraaminum cation with C₁₈ acyl and oligoethylene glycol, is identified as the most promising one from a variety of structurally diverse ILs, affording a 2.37-fold increase in octyl galactopyranoside yield compared to the buffer system. Up to 18.2 g L^–1 octyl galactopyranoside could be produced in 7 h, which is significantly higher than any previous report in terms of time-space efficiency. Kinetic study and COSMO-RS <i>in silico</i> predictions elucidate that the thermophilic nature of TN1577 β-galactosidase, increased solubility of substrate, suppression of hydrolysis, and excellent biocompatibility of Ammoeng 102 with enzyme (allowing TN1577 β-galactosidase to perform optimal catalysis up to 95 °C) are the main driving forces. The general applicability of the Ammoeng 102 system is verified, by which a series of alkyl galactopyranosides are successfully synthesized with <i>n</i>-butanol to <i>n</i>-tetradecanol as alkyl acceptors and lactose as galactosyl donor

Aspartic-Acid-Based Ampholytic Amphiphiles: Synthesis, Characterization, and pH-Dependent Properties at Air/Water and Oil/Water Interfaces

A facile and two-step strategy was employed to synthesize a series of novel aspartic-acid-based ampholytic amphiphiles from sustainable and commercially viable substances as starting materials. The molecular structures of the synthetic compounds were well-identified by mass spectrometry and 1H/13C nuclear magnetic resonance analysis, and the physicochemical, pH-dependent foaming, and emulsifying properties were evaluated by the use of multiple techniques, such as Fourier transform infrared spectroscopy, differential scanning calorimetry, Langmuir–Blodgett study, and fluorescence microscopy imaging. As a result of the co-existence of amino and carboxyl groups in the synthetic compounds, the compounds presented varying charges (cationic, ampholytic, and anionic) depending upon the pH of the medium compared to the dissociation constants (pKa). Compounds with cationic (pH 1.0) and anionic (pH 9.0) forms had significantly higher γ0.1 and critical micelle concentration values than those with ampholytic forms (pH 7.0). sn-1-Lauroyl-sn-3-aspartic acid (compound 3) at neutral and alkaline conditions displayed comparable foaming properties, including foaming, calcium-tolerant, and temperature-resistant abilities, with commercial sulfonate sodium dodecyl sulfate (SDS), and thus might be a promising alternative to SDS, applied in personal care products and detergent formula. sn-1-Palmtoyl-sn-3-aspartic acid (compound 5a) with an ampholytic structure was proven as the most excellent stabilizer for the preparation of oil-in-water emulsions compared to palmityl aspartic acid (compound 5b), commercial food ingredient diacetyltartaric acid esters of mono- and diglycerides, and glyceride monopalmitate at aqueous phase pH 7.0. Thus, it has promising use as a pH-dependent emulsifying agent in various fields