1. N-Acetylneuraminic acid aldolase-catalyzed synthesis of acyclic nucleoside analogues carrying a 4-hydroxy-2-oxoacid moiety
- Author
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Mariano J. Nigro, Elizabeth Sandra Lewkowicz, Martín Alejandro Palazzolo, Adolfo M. Iribarren, and Diego Damián Colasurdo
- Subjects
Stereochemistry ,Butyrate ,010402 general chemistry ,01 natural sciences ,Catalysis ,Nucleobase ,purl.org/becyt/ford/1 [https] ,chemistry.chemical_compound ,Aldol reaction ,purl.org/becyt/ford/1.4 [https] ,Moiety ,N-ACETYLNEURAMINIC ACID ALDOLASE ,chemistry.chemical_classification ,ACYCLIC NUCLEOSIDES ,biology ,010405 organic chemistry ,Process Chemistry and Technology ,Otras Ciencias Químicas ,Aldolase A ,Ciencias Químicas ,General Chemistry ,0104 chemical sciences ,Sialic acid ,Enzyme ,chemistry ,Oxoacid ,biology.protein ,CIENCIAS NATURALES Y EXACTAS ,ALDOL ADDITION - Abstract
N-Acetylneuraminic acid aldolase (NeuAcA) (EC 4.1.3.3) is a pyruvate-dependent class I aldolase that catalyzes the reversible aldol cleavage of N-acetylneuraminic acid to form N-acetyl-D-mannosamine and pyruvate. The synthetic activity of this enzyme has been applied to the preparation of many sialic acid analogues. In this report, we demonstrate the ability of NeuAcA from Clostridium perfringens to use 2-oxoethyl substituted nucleobases as unusual acceptor substrates to perform aldol additions. In this way, novel acyclic nucleoside analogues bearing a further derivatizable 4-hydroxy-2-oxo butyrate skeleton were prepared in good yields. Fil: Nigro, Mariano J.. Universidad Nacional de Quilmes; Argentina Fil: Palazzolo, Martín Alejandro. Universidad Nacional de Quilmes; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina Fil: Colasurdo, Diego Damián. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química. Laboratorio de Estudio de Compuestos Orgánicos; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata; Argentina Fil: Iribarren, Adolfo Marcelo. Universidad Nacional de Quilmes; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina Fil: Lewkowicz, Elizabeth Sandra. Universidad Nacional de Quilmes; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
- Published
- 2019