21007-21-6Relevant articles and documents
Hydrating the Bispropionate Notch in Malaria Pigment: A New Structural Motif in the Iron(III)(deuteroporphyrin) Dimer
Kuter, David,Suárez, Liliana,Dodd, Erin L.,Noll, Bruce C.,Stephens, Peter W.,Bohle, D. Scott
, p. 4373 - 4378 (2019)
Treating deuterohemin, chloro(deuteroporphyrinato)iron(III), with a non-coordinating base in DMSO/methanol allows for the isolation of [(deuteroporphyrinato)iron(III)]2, deuterohematin anhydride (DHA), an analogue of malaria pigment, the natural product of heme detoxification by malaria. The structure of DHA obtained from this solvent system has been solved by X-ray powder diffraction analysis and displays many similarities, yet important structural differences, to malaria pigment. Most notably, a water molecule of solvation occupies a notch created by the propionate side chains and stabilizes a markedly bent propionate ligand coordinated with a long Fe?O bond, and a carboxylate cluster associated with water molecules is generated. Together, these features account for its increased solubility and more open structure, with an increased porphyrin–porphyrin separation. The IR spectroscopic signature associated with this structure also accounts for the strong IR band at 1587 cm?1 seen for many amorphous preparations of synthetic malaria pigment, and it is proposed that stabilizing these structures may be a new objective for antimalarial drugs. The important role of the vinyl substituents in this biochemistry is further demonstrated by the structure of deuterohemin obtained by single-crystal X-ray diffraction analysis.
PORPHYRIN LINKED METRONIDAZOLE AGAINST GUM DISEASE: PORPHYROMONAS GINGIVALIS
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Page/Page column 29; 57, (2008/06/13)
The present invention relates generally to targeted molecular agents (TMAs) directed to a particular organism or group of organisms and uses thereof. More particularly, the present invention provides TMAs having a targeting moiety which comprises a natural or induced auxotrophic requirement of the particular organism as a vehicle for directing an agent linked to the moiety to be delivered to the target organism. The TMAs of the present invention are useful for targeting molecules such as antimicrobial agents and diagnostic agents to selected organisms.
Evidence for a Fast (Major) and Slow (Minor) Pathway in the Schumm Devinylation Reaction of Vinyl Porphyrins
DiNello, Robert K.,Dolphin, David H.
, p. 3498 - 3502 (2007/10/02)
The devinylation of protohemin in molten resorcinol is shown to proceed by two pathways.Two of the three possible intermediates in the minor (slow) pathway have been isolated and characterized as their dimethyl esters.In both, C-alkylation of resorcinol at the porphyrin C-1' vinyl side chains has occured.These intermediates are, however, converted into deuterohemin far too slowly for them to be on the major pathway from protohemin to deuterohemin.It is suggested that other intermediates, possibly in which O-alkylation of resorcinol has occurred, are intermediates in the major (fast) pathway from protohemin to deuterohemin.