The covalent immobilization of microsomal uridine diphospho-glucuronosyltransferase (UDPGT): Initial synthesis and characterization of an UDPGT immobilized enzyme reactor for the on-line study of glucuronidation

Kim, Hee Seung; Wainer, Irving W.

doi:10.1016/j.jchromb.2005.06.030

Cited by 19 publications

(18 citation statements)

References 23 publications

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“…Other alternatives could be the use of immobilized enzymes [10,20] or recombinant UDPGTs [13] but both of these methods are very laborious and/or expensive approaches. Moreover, it has been reported that the degree of conversion for the immobilized enzymes was lower than that in the reaction with the enzyme in solution and also the raw material cost would rise due to both a high uridine 5'-diphosphoglucuronic acid (UDPGA) consumption [10] and additional preparation of immobilized enzymes.…”

Section: Introductionmentioning

confidence: 99%

Biocatalyzed Synthesis and Structural Characterization of Monoglucuronides of Hydroxytyrosol, Tyrosol, Homovanillic Alcohol, and 3‐(4′‐Hydroxyphenyl)propanol

Khymenets¹,

Joglar²,

Clapés³

et al. 2006

Adv Synth Catal

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Abstract:The biocatalytic synthesis and purification of O-b-d-monoglucuronide conjugates of hydroxytyrosol, tyrosol, homovanillic alcohol, and 3-(4'-hydroxyphenyl)propanol, using porcine liver microsomes, are described here. The glucuronides were synthesized, analyzed and separated by HPLC-UV, identified by HPLC-MS, and their structures unequivocally established by NMR techniques. The outcome of the glucuronidation reaction depends on the structure of the phenolic compounds. Thus, the glucuronidation of hydroxytyrosol, biocatalyzed with porcine liver microsomes, proceeded exclusively on the phenolic hydroxy groups. The regioselectivity was similar to that observed for human and rat liver microsomes, the 4'-hydroxy position being more favorable than the 3'-hydroxy one. In the case of tyrosol, homovanillic alcohol, and hydroxyphenylpropanol, two products were formed during microsomal glucuronidation: a major one, the phenolic O-b-d-glucuronidated derivative and, a minor one, the O-b-d-glucuronidated aliphatic alcohol.

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Section: Introductionmentioning

confidence: 99%

Biocatalyzed Synthesis and Structural Characterization of Monoglucuronides of Hydroxytyrosol, Tyrosol, Homovanillic Alcohol, and 3‐(4′‐Hydroxyphenyl)propanol

Khymenets¹,

Joglar²,

Clapés³

et al. 2006

Adv Synth Catal

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“…Some alternative methods to microsome incubations have also been described where the UGT enzymes are adsorbed or covalently linked onto silica or to a monolithic carrier surface. There, the enzymes can be re-used many times or can continuously catalyze the glucuronidation reaction by a substrate flow-through technique called immobilized enzyme reactors (IMER) (Kim and Wainer 2005). The third approach is a bioproduction process, where specially modified strains of bacteria (for example Streptomyces sp.)…”

Section: Overview Of Glucuronide Quantification Approachesmentioning

confidence: 99%

Quantification of Glucuronide Metabolites in Biological Matrices by LC-MS/MS

Trontelj¹

2012

Tandem Mass Spectrometry - Applications and Principles

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“…1,2) IMERs have been used to study the enzymatic enantioselective recognition of racemic compounds 3) and the on-line synthesis and analysis of drug metabolites. 4,5) We have also previously prepared immobilized enzyme phospholipid columns with biomimetic characteristics for HPLC columns and examined their properties as enzyme reactors and their usage for drug development. 6) IMERs have been utilized in various applications combined with HPLC systems.…”

Section: Notesmentioning

confidence: 99%

Development of a Rapid and Detailed Structural Identification System with an On-Line Immobilized Enzyme Reactor Integrated into LC-NMR

Kashima

Okabayashi

2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Immobilized enzyme reactors (IMERs) integrated into an LC-NMR system were developed for rapid and detailed structural identification of enzymatic reaction products. An on-column enzymatic reaction was achieved for immobilized cytochrome-c and dog microsomes. After the reaction, these products were analyzed by LC-NMR without any work-up processes. The immobilized cytochrome-c column integrated into LC-NMR was used to characterize the reaction product formed on N-demethylation by measurement of

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The covalent immobilization of microsomal uridine diphospho-glucuronosyltransferase (UDPGT): Initial synthesis and characterization of an UDPGT immobilized enzyme reactor for the on-line study of glucuronidation

Cited by 19 publications

References 23 publications

Biocatalyzed Synthesis and Structural Characterization of Monoglucuronides of Hydroxytyrosol, Tyrosol, Homovanillic Alcohol, and 3‐(4′‐Hydroxyphenyl)propanol

Biocatalyzed Synthesis and Structural Characterization of Monoglucuronides of Hydroxytyrosol, Tyrosol, Homovanillic Alcohol, and 3‐(4′‐Hydroxyphenyl)propanol

Quantification of Glucuronide Metabolites in Biological Matrices by LC-MS/MS

Development of a Rapid and Detailed Structural Identification System with an On-Line Immobilized Enzyme Reactor Integrated into LC-NMR

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