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The synthesis of dihydropyrans with the D-xylo (1), D-ribo, L-arabino, and D-lyxo (2) configuration by one-carbon-atom homologation of D-mannose or D-galactose, terminal oxidation, and directed β elimination revealed (−)-daucic acid isolated from carrots to be 2, rather than 1 as previously thought. The identical configuration of 2 and KDO 8-P (3) and available biosynthetic information about chelidonic acid (4) suggest a KDO 8-P based pathway for the generation of 2 and 4 in plants.
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Lichtenthaler et al. (2003) studied this question.
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