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. Author manuscript; available in PMC: 2012 Apr 1.
Published in final edited form as: J Org Chem. 2011 Mar 3;76(7):2049–2055. doi: 10.1021/jo102277q

FIGURE 1.

FIGURE 1

A. [3H]BAB [3H]10 was radiochemically pure by TLC on untreated silica gel (20:80 EtOAc/hex, Rf = 0.51), Left Lane (20K DPM spotted) no carrier, Right Lane (20K DPM spotted) with 0.1 mg unlabeled carrier. The eluted, dried TLC plate was exposed to the PTR screen for 12 h. B. (Left Lane) The lipase-catalyzed deprotection of [3H]10 after 2 h 20 min (30K DPM spotted) showed 50% ester byproduct [3H]12 (Rf = 0.74) and 50% product radiolabeled 2-AG [3H]1 (Rf = 0.41) containing no rearrangement byproduct. (Right Lane) Flash chromatography gave product (27K DPM spotted) that contained 96% radiolabeled 2-AG [3H]1 (Rf = 0.41) and 4% rearrangement byproduct 1(3)-AG ([3H]2 + [3H]3) (Rf = 0.30). TLC was on boric acid treated silica gel (92.5:25:0.5:2 CHCl3/MeCOMe/HOAc/MeOH ) and the eluted, dried TLC plate was exposed to the PTR screen for 3 days. C. Analysis of the contour data from Plate B Right Lane to illustrate the high purity of the product radiolabeled 2-AG [3H]1.