Synthesis of Modified Thiopurine Nucleosides for Structural Characterization of Human Thiopurine S-Methyltransferase

Коршунова, Г. А.; Krynetski, Eugene Y.; Mtchedlidze, M. T.; Agapkin, Denis V.; Evans, William E.; Krynetskaia, Natalia F.

doi:10.1080/07328319908044839

Cited by 3 publications

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“…87 Thiopurines are of interest within the pharmaceutical industry as a result of the antiproliferate activity of these substrates, which has led to the use of these systems against leucoses. In order to study the active centre of thiopurine-S-methyl transferase, the principal determinant for the catabolism of thiopurines in humans, a series of photolabile thiopurines 88 (see 22 in Fig. 9) have been prepared and shown to be key substrates for the transferase enzyme.…”

Section: Diazirine Analogues Of Nucleotides and Nucleosides For Palmentioning

confidence: 99%

Development and application of diazirines in biological and synthetic macromolecular systems

2005

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Many different reagents and methodologies have been utilised for the modification of synthetic and biological macromolecular systems. In addition, an area of intense research at present is the construction of hybrid biosynthetic polymers, comprised of biologically active species immobilised or complexed with synthetic polymers. One of the most useful and widely applicable techniques available for functionalisation of macromolecular systems involves indiscriminate carbene insertion processes. The highly reactive and non-specific nature of carbenes has enabled a multitude of macromolecular structures to be functionalised without the need for specialised reagents or additives. The use of diazirines as stable carbene precursors has increased dramatically over the past twenty years and these reagents are fast becoming the most popular photophors for photoaffinity labelling and biological applications in which covalent modification of macromolecular structures is the basis to understanding structure-activity relationships. This review reports the synthesis and application of a diverse range of diazirines in macromolecular systems.

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Section: Diazirine Analogues Of Nucleotides and Nucleosides For Palmentioning

confidence: 99%

Development and application of diazirines in biological and synthetic macromolecular systems

2005

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Alkylating enzymes

Wessjohann¹,

Keim²,

Weigel³

et al. 2013

Current Opinion in Chemical Biology

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Chemospecific and regiospecific modifications of natural products by methyl, prenyl, or C-glycosyl moieties are a challenging and cumbersome task in organic synthesis. Because of the availability of an increasing number of stable and selective transferases and cofactor regeneration processes, enzyme-assisted strategies turn out to be promising alternatives to classical synthesis. Two categories of alkylating enzymes become increasingly relevant for applications: firstly prenyltransferases and terpene synthases (including terpene cyclases), which are used in the production of terpenoids such as artemisinin, or meroterpenoids like alkylated phenolics and indoles, and secondly methyltransferases, which modify flavonoids and alkaloids to yield products with a specific methylation pattern such as 7-O-methylaromadendrin and scopolamine.

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et al. 2000

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Synthesis of Modified Thiopurine Nucleosides for Structural Characterization of Human Thiopurine S-Methyltransferase

Abstract: Synthesis of a number of photoactive thiopurine-containing nucleosides was described. S-methylation of the synthesized compounds in the course of the reaction catalyzed by recombinant human thiopurine S-methyltransferase was studied by UV-spectroscopy.

Cited by 3 publications

References 1 publication

Development and application of diazirines in biological and synthetic macromolecular systems

Development and application of diazirines in biological and synthetic macromolecular systems

Alkylating enzymes

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