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The biosynthesis of shikimic acid from D-glucose.

P. R. Srinivasan,H. Shigeura,M. Sprecher,D. B. Sprinson,B. D. Davis

Published 1956 in Journal of Biological Chemistry

ABSTRACT

Shikimic acid (SA) is accumulated in the culture medium by certain bacterial mutants, which require for growth a mixture of tyrosine, phenylalanine, tryptophan, and several aromatic vitamins (1). Other strains, blocked in an earlier reaction in the same sequence, can utilize SA to replace these growth factors (1). SA has therefore been considered as an intermediate in the biosynthesis of these compounds. Similar observations have shown that 5-dehydroquinic acid (2) and 5-dehydroshikimic acid (3) are successive precursors of SA. The conclusion that these three substances are true intermediates has been further supported by the results of enzymatic studies (4, 5). Continued search for accumulated growth factors failed to reveal any earlier precursors. Meanwhile the early stages of this pathway have been investigated in other laboratories through observations on the conversion of certain labeled general carbon sources to tyrosine and phenylalanine (6-10). The interpretations of this work, however, have been limited by the fact that in these products of SA the two sides of the ring cannot be distinguished from each other. Since this distinction can be made in the non-aromatic ring of SA, we have investigated the formation of this substance from certain labeled compounds. The results indicate that with glucose as a sole carbon source 3 of the carbon atoms of SA are derived from glycolysis and the remaining 4 from the pentose phosphate pathway. Part of this work has been published in preliminary form (11, 12).

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