Solid-Phase Lipase-CuNPs Biohybrids as Catalysts for One-Pot Parallel Synthesis of 2,3,4-Triacetyl-D-Gluconic Acid

Losada-Garcia, Noelia ; Urriolabeitia, Esteban P. ; Palomo, Jose M.

Resumen: Solid-phase lipase/metal nanobiohybrids, generated by growth of copper nanoparticles on enzyme matrixes immobilized on graphene, were used as heterogeneous catalysts with dual-activity for the regioselective production of 2,3,4-triacetyl-D-gluconic acid from α-peracetylated-glucose in a one-pot parallel process combining a lipase-mediated regioselective hydrolytic monodeprotection with a metal-catalyzed oxidation in aqueous media. A novel synthetic strategy, based on the in situ fabrication of Cu nanoparticles induced by lipase molecules specifically immobilized on a multi-layer graphene material by interfacial adsorption fixing them in the active open conformation, has been described. Thermomyces lanuginosus lipase was firstly used to prepare the functionalized multi-layer graphene from graphite as a biographene preparation (Biographene, BIOG), support used to successfully immobilize Candida rugosa lipase (CRL). This immobilized form BIOG-CRL was further used to create successful active bifunctional enzyme-metal nanoarchitectures. Two different Cu-lipase hybrids were synthesised, where Cu species and nanoparticles size were different depending on the methodology. Regioselectivity and stability of the hybrids were evaluated successfully in the production of monosaccharide building blocks, besides the robustness of the hybrids in recyclability experiments. These findings highlight the potential of these solid-phase nanoarchitectures as useful tools in the synthesis of complex glycoderivatives for use in food, medicine, and cosmetics.

Idioma: Inglés

DOI: 10.1002/cctc.202201632

Año: 2023

Publicado en: ChemCatChem 15, 9 (2023), e202201632 [9 pp.]
ISSN: 1867-3880

Factor impacto JCR: 3.8 (2023)

Categ. JCR: CHEMISTRY, PHYSICAL rank: 74 / 178 = 0.416 (2023) - Q2 - T2

Factor impacto CITESCORE: 8.1 - Physical and Theoretical Chemistry (Q1) - Organic Chemistry (Q1) - Inorganic Chemistry (Q1) - Catalysis (Q2)

Factor impacto SCIMAGO: 1.034 - Inorganic Chemistry (Q1) - Physical and Theoretical Chemistry (Q1) - Organic Chemistry (Q1) - Catalysis (Q2)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E19-20R
Financiación: info:eu-repo/grantAgreement/EC/HORIZON EUROPE/101060130/EU/Twinning for intensified enzymatic processes for production of prebiotic-containing functional food and bioactive cosmetics/TwinPrebioEnz
Financiación: info:eu-repo/grantAgreement/ES/MICINN/PID2019-106394GB-I00

Tipo y forma: Article (Published version)