Tolyporphins L-R: Unusual Tetrapyrroles from a Brasilonema sp. of Cyanobacterium.

Joshua R Gurr, Jingqiu Dai, Casey S Philbin, Hope T Sartain, Timothy J O'Donnell, Wesley Y Yoshida, Arnold L Rheingold, Philip G Williams

The Journal of organic chemistry 2020 Jan 17

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Tolyporphins L-R (2-8) have been isolated from a mixed cyanobacterium-microbial culture. The structures of tolyporphins L and M have been revised to four constitutional isomers, isolated as two mixtures of dioxobacteriochlorins (2/3 and 4/5). In contrast, tolyporphin P (6) is a fully oxidized tetrapyrrole, while tolyporphins Q and R (7 and 8) are oxochlorins. X-ray structures are reported for the first time for tolyporphins A (1), R (8), and E (9), revealing unexpected stereochemical variation within the series.

Citation

Joshua R Gurr, Jingqiu Dai, Casey S Philbin, Hope T Sartain, Timothy J O'Donnell, Wesley Y Yoshida, Arnold L Rheingold, Philip G Williams. Tolyporphins L-R: Unusual Tetrapyrroles from a Brasilonema sp. of Cyanobacterium. The Journal of organic chemistry. 2020 Jan 17;85(2):318-326