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Biosynthesis of pyrrolnitrin. Incorporation of 13C, 15N double-labelled D- and L-tryptophan

✍ Scribed by Pei Zhou; Ursula Mocek; Brian Siesel; Prof. Dr. Heinz G. Floss

Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
399 KB
Volume
32
Category
Article
ISSN
0233-111X

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✦ Synopsis

Experiments on the incorporation of D-and ~-[alanine-3-'~C,2-''N]tryptophan into the antibiotic pyrrolnitrin in Pseudomonas aureofaciens confirmed earlier conclusions about the conversion of L-tryptophan into pyrrolnitrin. They also demonstrated that a fraction of the D isomer is incorporated without breakage of the "N-carbon bond, consistent with the operation of a second pathway from D-tryptophan to pyrrolnitrin. Cell-free experiments confirmed the conversion of 3-(o-aminophe-ny1)pyrrole into aminopyrrolnitrin but failed to detect enzymatic oxidation of the latter to pyrrolnitrin. The clinically used antifungal antibiotic, pyrrolnitrin (1) (ARIMA et al., 1965), a metabolite of Pseudomonaspyrrocinia (IMANAKA et al., 1965) and other Pseudomonas species (ELANDER et al., 1968), is derived from the amino acid, tryptophan (GORMAN and LIVELY 1967). Based on extensive tracer experiments we (CHANG et al., 1981) have proposed the biosynthetic pathway shown in Fig. 1 . The postulated skeletal rearrangement is firmly supported by r 1 2 QJ-pCooH] H -0-0 NH, H 3 NHZ H CI 4 P. ZHOU et ul.

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