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. 2016 Feb 4;7:10622. doi: 10.1038/ncomms10622

Figure 2. Synthesis of photocaged 5-InsP7 and mechanism of LevB cleavage.

Figure 2

(a) Synthesis of DEACM 5–InsP7 9 and 5-InsP7 10 based on fluorenylmethyl (Fm) protection and a novel phosphate-protecting group (LevB). DCI, 4,5-dicyanoimidazole; DEACM, [7-(diethylamino)-coumarin-4-yl]methyl; Fm, fluorenylmethyl; mCPBA, metachloro perbenzoic acid; TFA, trifluoroacetic acid. (b) An adaptor strategy for phosphate release: hydrazine triggers levulinate (red) cleavage and 1,6-elimination (blue) to release free phosphate. Generally, levulinate could also be replaced with other phenol protecting groups.