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Syntetyczne odpowiedniki fosfoenolopirogronianu, czyli jak naśladować biosyntezę kwasów ulozonowych

Molenda M. A.

Wiadomości Chemiczne

2014

[Z] 68, 9-10

873--896

Ulosonic acids are key intermediated in many important biochemical pathways. One of them is DAH, which takes part in the shikimic acid pathway, as precursor in aromatic amino acids biosynthesis [1]. Another interesting compound is KDN isolated from rainbow trout egg [2], where it is responsible for the protection of the embryo in the early stages of embryonic development [3]. In the nature ulosonic acids are synthesized from phosphorylated sugar aldehydes and phosphoenolpyruvate in enzymatic aldol reaction. Mimic of enzymatic catalysis by asymmetric direct aldol reaction is one of the challenges of modern organic synthesis. Unfortunately, installation of the pyruvate unit in laboratory conditions is quite problematic. The aim of this short review was to present synthetic equivalents of phosphoenolpyruvate, which over the years become more and more similar to the biosynthesis of ulosonic acids in living cells. The first applied pyruvic acid unit was 2-acethylthiazole used as stoichiometric lithium enolate in aldol addition [9]. Next, the same research group used the phosphine derivative of 2-acethylthiazole in Wittig olefination of sugar aldehydes with subsequent stereoselective syn Michael addition of the benzyl oxide anion. Another puryvate equivalent is dimethyl acetal of pyruvic aldehyde successfully used in organocatalytic [12] and metalorganocatalytic [14] direct aldol reactions. Nowadays sterically hindered aromatic ester of pyruvic acid is probably the best puryvate unit. This ester was successfully used as aldol reaction donor in synthesis of two 3-deoxy-2-ulosonic acids – KDG and KDO [18]. Aryl pyruvate reacts with aldehydes to give aldol product with high efficiency and good diastereoselectivity in reaction catalyzed by chiral tertiary amines represented by Cinchona alkaloids. Chiral sugar aldehydes and pyruvate ester, are the building blocks that famously mimic the biological precursors of ulosonic acids.