TOTAL SYNTHESIS OF COLNELEIC ACID

The lipoxygenase of potato (Solarium tuberosum) converts endogenous linoleic acid to a mixture of 9(S)- and 13(S)-hydroperoxides.1 The 9(S)-hydroperoxide 2 is transformed further by lipoxygenase preparations from potato homogenate under anaerobic conditions to colneleic acid, 1, an unusual fatty acid which can be isolated from potato tubers.2 Although the physiological function of colneleic acid in S. tuberosum is unknown, the surmise that it might be an important biochemical regulator was rendered more plausible by the finding in this laboratory that 1 is a strong competitive inhibitor of the potato lip-oxygenase (Ki at 23 °C and pH 6.3 of 7 μM).3 For example, it is not unreasonable that hte potato lipoxygenase under regulation by its own product (1) could function as an oxygen sensor which links metabolism and oxygen supply. © 1990, American Chemical Society. All rights reserved.