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Volume 271, Number 47, Issue of November 22, 1996 pp. 29652-29658
©1996 by The American Society for Biochemistry and Molecular Biology, Inc.

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Polyprenylphosphate-pentoses in Mycobacteria Are Synthesized from 5-Phosphoribose Pyrophosphate

(Received for publication, June 27, 1996, and in revised form, August 16, 1996)

From the Department of Microbiology, Colorado State University, Fort Collins, Colorado 80523

Polyprenylphosphate-arabinose (in which the polyprenyl unit is found both as decaprenyl and octahydroheptaprenyl) is a donor of mycobacterial cell wall arabinosyl residues. Because of this important role, its biosynthetic pathway, and that of the related lipid, polyprenylphosphate-D-ribose, was investigated. Surprisingly, phosphoribose pyrophosphate was shown to be a key intermediate on the pathway to both polyprenylphosphate-D-pentoses. Thus, incubation of 5-phospho-D-[¹⁴C]ribose pyrophosphate with membranes prepared from Mycobacterium smegmatis resulted in the presence of organic-soluble radioactivity that was shown to be, in part, polyprenylphosphate-[¹⁴C]arabinose and polyprenylphosphate-[¹⁴C]ribose. Two additional intermediates, polyprenylphosphate-5-phospho[¹⁴C]ribose and polyprenylphosphate-5-phospho[¹⁴C]arabinose, were identified. Further experiments showed that the mature polyprenylphosphate-ribose is formed from phosphoribose pyrophosphate via a two-step pathway involving a transferase to form polyprenylphosphate-5-phosphoribose and then a phosphatase to form the final polyprenylphosphateribose. Polyprenylphosphate-arabinose is formed by a similar pathway with an additional step being the epimerization at C-2 of the ribosyl residue. This epimerization occurs at either the level of phosphoribose pyrophosphate or at the level of polyprenylphosphate-5-phosphoribose.

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