✦ LIBER ✦

The biosynthesis of streptonigrin from [1-13C]-D-erythrose

✍ Scribed by William J Gerwick; Steven J Gould; Hossein Fonouni

Publisher: Elsevier Science
Year: 1983
Tongue: French
Weight: 186 KB
Volume: 24
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)94108-x

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✦ Synopsis

Twelve of the twenty-five carbon atoms of streptonigrin are derived from three intact erythrose units. We reported4 that feeding [U-13 C6]-D-glucose (1) to growing cultures of Streptomyces flocculus ATCC 13257 yielded streptonigrin specifically labeled at all carbons. An analysis of the 13 13 C-C spin coupling patterns making use of 13 C-13 C homonuclear decoupling experiments revealed the size and location of each of the primary precursors, as shown in structure 2%.

HO 4 H.,N, ,COOH 0CH3 2a _.., 3

The labeling pattern of the C-D rings was fully consistent with their known5 derivation from B-methyl tryptophan (3), while the C4+C2 pattern of the A-ring was consistent with its derivation from a shikimate-type pathway. In total, three C4 biogenetic units were clearly involved in streptonigrin biosynthesis. We now present evidence that all three C4 units are derived from D-erythrose-4-phosphate (4).

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