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A Streptomyces Cytochrome P450 Enzyme Catalyzes Regiospecific C2-Guaninylation for the Synthesis of Diverse Guanitrypmycin Analogs

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JOURNAL OF NATURAL PRODUCTS
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AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.2c00787

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Heterologous expression of a cdps-p450 locus from Streptomyces sp. NRRL S-1521 led to the identification of a new guaninylated diketopiperazine, guanitrypmycin D1. The cytochrome P450 GutD1521 catalyzes the regiospecific transfer of guanine to C-2 of the indole ring of cyclo-(L-Trp-L-Tyr) via a C-C linkage, representing a new chemical transformation within this enzyme class. Furthermore, GutD1521 efficiently accepts several other tryptophan-containing cyclodipeptides or derivatives for regiospecific coupling with guanine, thus generating different guanitrypmycin analogs.
Heterologous expression of a cdps-p450 locus from Streptomyces sp. NRRL S-1521 led to the identification of guanitrypmycin D1, a new guaninylated diketopiperazine. The cytochrome P450 GutD1521 catalyzed the regiospecific transfer of guanine to C-2 of the indole ring of cyclo-(L-Trp-L-Tyr) via a C-C linkage and represents a new chemical transformation within this enzyme class. Furthermore, GutD1521 efficiently accepts several other tryptophan-containing cyclodipeptides or derivatives for regiospecific coupling with guanine, thus generating different guanitrypmycin analogs.

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