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Cholesteryl diazoacetate (1), a potential membrane photolabeling reagent, has been incorporated into dipalmitoylphosphatidylcholine (DPPC) small unilamellar vesicles (SUV). Immobilization of the photolabel within the bilayer matrix was demonstrated by super(13)C and super(1)H NMR and was found to be closely analogous to that of cholesterol. SUV composition was verified by integration of proton NMR resonances from CDCl sub(3) solutions of chloroform extracts of vesicle preparations. These intermolecular C-H and O-H insertions indicate that the photogenerated carbene from 1 is situated at the aqueous inteface of the membrane, analogously to the known orientation of the OH group of cholesterol.