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Please use this identifier to cite or link to this item: https://hdl.handle.net/20.500.12008/47580 How to cite
Title: Synthesis of chiral acyclic pyrimidine nucleoside analogues from DHAP-dependent aldolases
Authors: Nigro, Mariano
Sánchez-Moreno, Israél
Benito-Arenas, Raúl
Valino, Ana L.
Iribarren, Adolfo M.
Veiga, Nicolás
García-Juneda, Eduardo
Lewkowicz, Elizabeth, S.
Type: Artículo
Descriptors: BIOCATALISIS, FARMACOLOGIA, ALDOLASAS
Issue Date: 2024
Abstract: Dihydroxyacetone phosphate (DHAP)-dependent aldolases catalyze the aldol addition of DHAP to a variety of aldehydes and generate compounds with two stereocenters. This reaction is useful to synthesize chiral acyclic nucleosides, which constitute a well-known class of antiviral drugs currently used. In such compounds, the chirality of the aliphatic chain, which mimics the open pentose residue, is crucial for activity. In this work, three DHAP-dependent aldolases: fructose- 1,6-biphosphate aldolase from rabbit muscle, rhanmulose-1-phosphate aldolase from Thermotoga maritima, and fuculose-1-phosphate aldolase from Escherichia coli, were used as biocatalysts. Aldehyde derivatives of thymine and cytosine were used as acceptor substrates, generating new acyclic nucleoside analogues containing two new stereocenters with conversion yields between 70% and 90%. Moreover, structural analyses by molecular docking were carried out to gain insights into the diasteromeric excess observed.
Publisher: MDPI
IN: Biomolecules. 2024 14(7), e750
Citation: Nigro, M, Sánchez-Moreno, I, Benito-Arenas, R, Valino, A, Iribarren, A, Veiga, N, García-Juneda, E y Lewkowicz, E. "Synthesis of chiral acyclic pyrimidine nucleoside analogues from DHAP-dependent aldolases". Biomolecules [en línea] 2024 14(7), e750
Appears in Collections:Publicaciones académicas y científicas - Facultad de Química

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