Quorum sensing (QS) in bacteria is the behavior of intercellular communications that permit cells to adjust gene expression based on cell population. QS-2 responds to AI-2, which is produced by the enzyme LuxS and substrate S-ribosylhomocysteine (SRH). SRH is comprised of two moieties: a ribose component and a four-carbon amino acid component. Current synthetic processes involve using a homocysteine derivative as a nucleophile and a ribose derivative as an electrophile in an SN2 reaction to produce the thioether bond of SRH. Here, the synthetic route of interest is instead a potentially more efficient SN2 reaction using a homoserine derivative as the electrophile and a ribose derivative as the nucleophile. Both nucleophile and electrophile can be synthesized through standard organic transformations. The electrophile precursor involves first synthesizing a key intermediate, Boc-Asp-OtBu, from L-aspartic acid through four transformations, the order of which was critical. A single purification step was completed only for intermediate Boc-Asp(OMe)-OtBu, which was later saponified. Boc-Asp-OtBu can be taken further forward to synthesize protected homoserine derivatives (i.e., sulfonates, halides). These derivatives are used for incorporation with thiol ribose into the SRH molecule, with possible future application into the synthesis of SRH analogs.?

Alternate approach to the synthesis of <i>?S</i>?-ribosylhomocysteine (SRH)

248th National Meeting (2014)

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Alternate approach to the synthesis of ?S?-ribosylhomocysteine (SRH)