The Stereochemistry of α‐Oxidation of Fatty Acids in Plants

Abstract

When [1‐ 14 C]palmitic acid is incubated with young pea leaves, or solutions of their acetonedried powders, d ‐2‐hydroxy[1‐ 14 C]palmitic acid accumulates. When l ‐[1‐ 14 C, 2‐ 3 H]palmitic acid is similarly oxidised, d ‐2‐hydroxy[1‐ 14 C]palmitate is formed which retains the tritium (99% retention). When d ‐[1‐ 14 C, 2‐ 3 H]palmitic acid is similarly oxidised, d ‐2‐hydroxy [1‐ 14 C]palmitate is formed with loss of tritium (24% retention). The mechanism of α‐hydroxylation is therefore replacement of α‐hydrogen by hydroxyl with overall retention of configuration.