<i>Aeromonas hydrophila</i>strains as biocatalysts for transglycosylation

Nóbile, Matías L.; Terreni, Marco; Lewkowicz, Elizabeth Sandra; Iribarren, Adolfo M.

doi:10.3109/10242422.2010.538949

Cited by 14 publications

(8 citation statements)

References 21 publications

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“…Syntheses of adenine nucleosides, such as 2-fluoro-2 -deoxyadenosine 2a [4][5][6][7] and 2-fluoroadenosine 2b [6,8] have been demonstrated through different approaches. Introduction of fluorine to the C-8 position of purine nucleosides is more challenging, likely due to the instability of the resulting nucleosides.…”

Section: Resultsmentioning

confidence: 99%

8-Fluoro-N-2-isobutyryl-2′-deoxyguanosine: Synthesis and Reactivity

Solodinin

Helmkay

Ollivier

et al. 2020

Molbank

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3 ,5 -O-Bis(tert-butyldimethylsilyl)-8-fluoro-N-2-isobutyryl-2 -deoxyguanosine was synthesized from 3 ,5 -O-bis(tert-butyldimethylsilyl)-N-2-isobutyryl-2 -deoxyguanosine by the treatment with N-fluorobenzenesulfonimide. A similar fluorination reaction with 3 ,5 -O-bis(tert-butyldimethylsilyl)-N-2-(N,N-dimethylformamidine)-2 -deoxyguanosine, however, failed to give the corresponding fluorinated product. It was found that 8-fluoro-N-2-isobutyryl-2 -deoxyguanosine is labile under acidic conditions, but sufficiently stable in dichloroacetic acid used in solid phase synthesis. Incorporation of 8-fluoro-N-2-isobutyryl-2 -deoxyguanosine into oligonucleotides through the phosphoramidite chemistry-based solid phase synthesis failed to give the desired products. Furthermore, treatment of 8-fluoro-N-2-isobutyryl-2 -deoxyguanosine with aqueous ammonium hydroxide did not give 8-fluoro-2 -deoxyguanosine, but led to the formation of a mixture consisting of 8-amino-N-2-isobutyryl-2 -deoxyguanosine and C8:5 -O-cyclo-2 -deoxyguanosine. Taken together, an alternative N-protecting group and possibly modified solid phase synthetic cycle conditions will be required for the incorporation of 8-fluoro-2 -deoxyguanosine into oligonucleotides through the phosphoramidite chemistry-based solid phase synthesis.

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Section: Resultsmentioning

confidence: 99%

8-Fluoro-N-2-isobutyryl-2′-deoxyguanosine: Synthesis and Reactivity

Solodinin

Helmkay

Ollivier

et al. 2020

Molbank

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“…Chemoenzymatic approaches (a, b, c) to prepare Abacavir from Diels-Alder cycloaddition of cyclopentadiene. and agarose-entrapped whole cells (Nóbile et al, 2010), as well as cloned and overexpressed free enzymes (Ubiali et al, 2012), thermostable Geobacillus stearothermophilus (De Benedetti et al, 2012) and Aeropyrum pernix K1 (Zhu et al, 2013).…”

Section: As Nucleoside Prodrugsmentioning

confidence: 99%

Biocatalytic approaches applied to the synthesis of nucleoside prodrugs

Iglesias

Lewkowicz

Médici

et al. 2015

Biotechnology Advances

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“…We have prepared purine dNs by biocatalyzed transglycosylation using nucleoside phosphorylases (NPs) or whole cells that contain these enzymes in a one-pot cascade reaction [9][10][11]. This methodology requires pyrimidine dNs as starting materials and proceeds through the formation of the corresponding α-furanose 1-phosphate (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Selection of a New Whole Cell Biocatalyst for the Synthesis of 2-Deoxyribose 5-Phosphate

Valino

Palazzolo

Iribarren

et al. 2011

Appl Biochem Biotechnol

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2-deoxyribose 5-phosphate (DR5P) is a key intermediate in the biocatalyzed preparation of deoxyribonucleosides. Therefore, DR5P production by means of simpler, cleaner, and economic pathways becomes highly interesting. One strategy involves the use of bacterial whole cells containing DR5P aldolase as biocatalyst for the aldol addition between acetaldehyde and D: -glyceraldehyde 3-phosphate or glycolytic intermediates that in situ generate the acceptor substrate. In this work, diverse microorganisms capable of synthesizing DR5P were selected by screening several bacteria genera. In particular, Erwinia carotovora ATCC 33260 was identified as a new biocatalyst that afforded 14.1-mM DR5P starting from a cheap raw material like glucose.

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Aeromonas hydrophilastrains as biocatalysts for transglycosylation

Cited by 14 publications

References 21 publications

8-Fluoro-N-2-isobutyryl-2′-deoxyguanosine: Synthesis and Reactivity

8-Fluoro-N-2-isobutyryl-2′-deoxyguanosine: Synthesis and Reactivity

Biocatalytic approaches applied to the synthesis of nucleoside prodrugs

Selection of a New Whole Cell Biocatalyst for the Synthesis of 2-Deoxyribose 5-Phosphate

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