Core chromophores of native photosynthetic pigments

Lindsey, Jonathan S.; Taniguchi, Masahiko

doi:10.1016/b978-0-323-98391-4.00021-6

Cited by 1 publication

(1 citation statement)

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“…The semisynthetic reactions of tolyporphins to date include O -acetylation, O -deacetylation, O -butanoylation, metal chelation, and ketone reduction; the totality of such reactions pales against that known for native bacteriochlorophylls. Synthetic routes to gem-dialkyl-substituted chlorins and bacteriochlorins are available [ 218 ], but much remains to be done to accommodate the peripheral substituents that adorn the various tolyporphins. Efficacious access to an abundance of each member of the repertoire of tolyporphins, including precursors and analogues and derivatives, would open doors to study biosynthesis and physiology.…”

Section: Perspectivementioning

confidence: 99%

Tolyporphins–Exotic Tetrapyrrole Pigments in a Cyanobacterium—A Review

Nguyen,

Zhang,

Liu

et al. 2023

Molecules

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Tolyporphins were discovered some 30 years ago as part of a global search for antineoplastic compounds from cyanobacteria. To date, the culture HT-58-2, comprised of a cyanobacterium–microbial consortium, is the sole known producer of tolyporphins. Eighteen tolyporphins are now known—each is a free base tetrapyrrole macrocycle with a dioxobacteriochlorin (14), oxochlorin (3), or porphyrin (1) chromophore. Each compound displays two, three, or four open β-pyrrole positions and two, one, or zero appended C-glycoside (or –OH or –OAc) groups, respectively; the appended groups form part of a geminal disubstitution motif flanking the oxo moiety in the pyrroline ring. The distinct structures and repertoire of tolyporphins stand alone in the large pigments-of-life family. Efforts to understand the cyanobacterial origin, biosynthetic pathways, structural diversity, physiological roles, and potential pharmacological properties of tolyporphins have attracted a broad spectrum of researchers from diverse scientific areas. The identification of putative biosynthetic gene clusters in the HT-58-2 cyanobacterial genome and accompanying studies suggest a new biosynthetic paradigm in the tetrapyrrole arena. The present review provides a comprehensive treatment of the rich science concerning tolyporphins.

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Section: Perspectivementioning

confidence: 99%