Utilize este identificador para referenciar este registo: https://hdl.handle.net/1822/91445

TítuloSolvent-free synthesis of hydrophobic and amphiphilic esters using a chemically modified lipase from thermomyces lanuginosus: a comparative study with native and immobilized forms
Autor(es)Roque, Catarina S.
Castro, Mariana de
Castro, Tarsila G.
Silva, C.
Cavaco-Paulo, Artur
Noro, Jennifer Martins
Palavras-chaveEsterification
Solvent-free
Chemically modified lipase
Amphiphilic esters
Data16-Fev-2024
EditoraWiley-Blackwell
RevistaChembiochem
CitaçãoRoque, Catarina; Castro, Mariana; Castro, T.; Silva, Carla; Cavaco-Paulo, Artur; Jennifer Noro, Solvent-free synthesis of hydrophobic and amphiphilic esters using a chemically modified lipase from Thermomyces lanuginosus: a comparative study with native and immobilized forms. ChemBioChem, 25(4), e202300843, 2024
Resumo(s)Using lipases to catalyze the synthesis of the most differentiated type of compounds remains one of the major challenges among scientists. Seeking more economic and advantageous catalysts is a current goal of green chemistry. In this work, we demonstrate the potential of a chemically modified form of lipase from Thermomyces lanuginosus (cmLTL) for the synthesis of both hydrophobic (heptyl heptanoate, heptyl octanoate, heptyl decanoate, decyl heptanoate, decyl octanoate and decyl decanoate) and amphiphilic (2-(2-ethoxyethoxy)ethyl oleate and 2-(2-ethoxyethoxy)ethyl linoleate) esters, in bulk. The results were compared with its native (LTL) and immobilized (imLTL) forms. The data revealed that LTL showed poor activity for all reactions performed with n-heptane (<20\%). ImLTL was able to synthesize all hydrophobic esters (>60\%), with exception of the short ester, heptyl heptanoate. cmLTL was the only form of LTL capable of producing hydrophobic and amphiphilic esters, without compromising the yield when the reactions were performed under solvent-free conditions (>50\%). Molecular modeling showed that the active pocket of cmLTL is able to deeply internalize transcutol, with stronger interactions, justifying the outstanding results obtained. Furthermore, owing to the possibility of cmLTL filtration, the reusability of the catalyst is ensured for at least 6 cycles, without compromising the reaction yields.
TipoArtigo
URIhttps://hdl.handle.net/1822/91445
DOI10.1002/cbic.202300843
ISSN1439-4227
Versão da editorahttps://chemistry-europe.onlinelibrary.wiley.com/journal/14397633
Arbitragem científicayes
AcessoAcesso aberto
Aparece nas coleções:CEB - Publicações em Revistas/Séries Internacionais / Publications in International Journals/Series

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