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Crystal structures of the two enantiomers of cis-2 bound to nNOS. (3S,4S)-2 (3JWS) binds as expected with the aminopyridine positioned over the heme near Glu592. However, (3R,4R)-2 (3JWT) binds in the flipped mode which places the aminopyridine near a heme propionate. This requires Tyr706 to adopt the “out” rotamer conformation.
