Protein prenylation is a critical post-translational modification required for the normal function of many proteins involved in mediating processes such as cell division and growth. Understanding and controlling these processes within the cellular environment are paramount to comprehending normal cell physiology, as well as abnormal or diseased-state cell physiology. Elucidation of these pathways has been assisted by the use of photolabile protecting groups (PPGs) for thiols essential to prenylation. PPGs are removed via either one- or two-photon excitation to reveal the thiol. Nitrodibenzofuran (NDBF) has been shown to be an effective PPG for such applications. To extend the utility of NDBF, we designed and performed the synthesis of dimethylamine-functionalized nitrodibenzofuran (aNDBF). The electron-donating amine group results in a significantly longer wavelength absorption (100 nm). When used in conjunction with NDBF, aNDBF may allow for selective, orthogonal thiol-uncaging in the same sample. The optimized synthetic route to aNDBF from commercially available dibenzofuran will be described, including the key installation of the dimethylamine functionalization onto the NDBF scaffold. One- and two-photon uncaging properties were characterized, and special efforts were taken to characterize the two-photon uncaging efficiency at 700 nm, 800 nm and 900 nm and compared with those of NDBF. A greater understanding of the capabilities of these orthogonal PPGs and their properties incentivizes further studies to continue the elucidation of prenylation mediated cellular signaling.<br/>

Nitrodibenzofuran photoactivatable protecting group with longer wavelength absorption for orthogonal activation of biological thiols

255th National Meeting (2018)

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