Regioselective enzymatic aminoacylation of lobucavir to give an intermediate for lobucavir prodrug

Hanson, Ronald L.; Shi, Zugui; Brzozowski, David B.; Banerjee, Amit; Kissick, Thomas P.; Singh, Jagadish; Pullockaran, Annie; North, Jeffrey T.; Fan, Junying; Howell, J. M.; Durand, Susan C.; Montana, Michael A.; Kronenthal, David R.; Mueller, Richard H.; Patel, Ramesh N.

doi:10.1016/s0968-0896(00)00209-1

Cited by 40 publications

(11 citation statements)

References 10 publications

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“…A prodrug 29 in which one of the two hydroxyls is coupled to valine has also been considered for development. Regioselective aminoacylation, difficult to achieve by chemical procedures, appeared to be suitable for an enzymatic approach [27]. Synthesis of the lobucavir L-valine prodrug 29 requires regioselective coupling of one of the two hydroxyl groups of lobucavir (27) with valine.…”

Section: Regioselective Enzymatic Aminoacylationmentioning

confidence: 99%

“…Regioselective aminoacylation, difficult to achieve by chemical procedures, appeared to be suitable for an enzymatic approach [27]. Synthesis of the lobucavir L-valine prodrug 29 requires regioselective coupling of one of the two hydroxyl groups of lobucavir (27) with valine. Enzymatic processes were developed for aminoacylation of either hydroxyl group of lobucavir [27].…”

Section: Regioselective Enzymatic Aminoacylationmentioning

confidence: 99%

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Biocatalysis: Synthesis of Chiral Intermediates for Pharmaceuticals

Patel¹

2006

COC

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Abstrct:The production of single enantiomers of drug intermediates has become increasingly important in the pharmaceutical industry. Chiral intermediates and fine chemicals are in high demand by both the pharmaceutical and agrochemical industries for the preparation of bulk drug substances and agricultural products. The enormous potential of microorganisms and enzymes for the transformation of synthetic chemicals with high chemo-, regio-and enatioselectivities has been demonstrated. In this article, biocatalytic processes are described for the synthesis of chiral intermediates for anti-hypertensive drugs, lipid lowering drugs, anti-cancer agents, antiviral agents, β-3-and β-2-receptor receptor agonists, melatonin receptor agonists, a tryptase inhibitor, retinoic acid γ-specific antagonist, and antiAlzheimer's drugs. Enzymatic acyloin condensation and carbobenzyloxy group deprotection reactions are also described.

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Section: Regioselective Enzymatic Aminoacylationmentioning

confidence: 99%

Section: Regioselective Enzymatic Aminoacylationmentioning

confidence: 99%

Biocatalysis: Synthesis of Chiral Intermediates for Pharmaceuticals

Patel¹

2006

COC

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“…The lobucavir pro-drug L-valine [1S,2R,3R)-3-(2--amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-2-(hydroxymethyl)cyclobutyl]methyl ester monohydrochloride 22, in which one of the two hydroxyls is coupled to valine, has also been considered for development. Regioselective aminoacylation was difficult to achieve by chemical procedures but appeared to be suitable for an enzymatic approach (24). Synthesis of the lobucavir pro-drug 22 required regioselective coupling of one of the two hydroxyl groups of lobucavir with valine.…”

Section: Lobucavirmentioning

confidence: 99%

“…Synthesis of the lobucavir pro-drug 22 required regioselective coupling of one of the two hydroxyl groups of lobucavir with valine. Enzymatic processes were developed for the aminoacylation of either hydroxyl group of lobucavir (24). The selective hydroly- Ribavirin pro-drug…”

Section: Lobucavirmentioning

confidence: 99%

Biocatalytic Synthesis of Chiral Pharmaceutical Intermediates

Patel

2005

ChemInform

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SummaryThe production of single enantiomers of drug intermediates has become increasingly important in the pharmaceutical industry. Chiral intermediates and fine chemicals are in high demand from both the pharmaceutical and agrochemical industries for the preparation of bulk drug substances and agricultural products. The enormous potential of microorganisms and enzymes for the transformation of synthetic chemicals with high chemo-, regio-and enantioselectivities has been demonstrated. In this article, biocatalytic processes are described for the synthesis of chiral pharmaceutical intermediates.

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“…Ferrero & Gotor (2000) reviewed the utility of biocatalysts for the modification of nucleosides, carbocyclic nucleosides, and C-nucleosides. Hanson et al (2000) reported the lipase-catalyzed synthesis of the pro-drug of lobucavir, which is a nucleoside analogue used as an antiviral agent for treatment of herpes viruses and hepatitis B.…”

Section: Introductionmentioning

confidence: 99%

Regioselective enzymatic acylation of ribavirin to give potential multifunctional derivatives

Liu

Wang

et al. 2005

Biotechnol Lett

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Lipase-catalyzed synthesis of potential multifunctional ribavirin derivatives was performed in acetone. Divinyl dicarboxylates with different chain lengths (C4, C6, C9, C10) were used as acyl donors and the reactions were catalyzed by lipase immobilized on acrylic resin from Candida antarctica (CAL-B). Ribavirin was regioselectivly acylated at the primary hydroxyl groups and the corresponding vinyl esters (C4, C6, C9, C10) were prepared in respective yields of 48%, 65%, 54%, 55%.

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Regioselective enzymatic aminoacylation of lobucavir to give an intermediate for lobucavir prodrug

Cited by 40 publications

References 10 publications

Biocatalysis: Synthesis of Chiral Intermediates for Pharmaceuticals

Biocatalysis: Synthesis of Chiral Intermediates for Pharmaceuticals

Biocatalytic Synthesis of Chiral Pharmaceutical Intermediates

Regioselective enzymatic acylation of ribavirin to give potential multifunctional derivatives

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