Biological methylation plays a vital role in cellular function due to its involvement in replication and metabolism. Methylation is carried out by methyltransferases and requires the native donor, S-adenosyl-L-methionine (SAM). This work focuses on the synthesis of SAM analogues functionalized at the N6-position with a variety of azides and alkynes that will function as probes of biological methylation. Specifically, the analogues described here will facilitate future studies of biological methylation through the incorporation of fluorophores or affinity tags via Click Chemistry. The work described here outlines the synthetic progress towards generating a specific subclass of amide-based analogues. A novel approach is being used to expand the library of molecules which involves the synthesis of a common intermediate compound that allows for facile diversification at the desired N6-position. The synthesis of 1 has been optimized and the compound can be obtained in good yield. Current work is focused on the synthesis of the requisite acid chlorides and subsequent acylation to give 2a-e.

Synthesis of novel N6-substituted S-adenosyl-L-methionine analogues

254th National Meeting (2017)

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