978-24-5Relevant articles and documents
Functionalized expanded porphyrins
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Page/Page column 13; 14, (2013/11/19)
Disclosed are functionalized expanded porphyrins that can be used as spectrometric sensors for high-valent actinide cations. The disclosed functionalized expanded porphyrins have the advantage over unfunctionalized systems in that they can be immobilized
Immobilization of a hexaphyrin(1.0.1.0.0.0) derivative onto a tentagel-amino resin and its use in uranyl cation detection
Melfi, Patricia J.,Camiolo, Salvatore,Lee, Jeong Tae,Ali, Mehnaaz F.,McDevitt, John T.,Lynch, Vincent M.,Sessler, Jonathan L.
, p. 1538 - 1540 (2008/09/20)
The synthesis of an isoamethyrin derivative containing two CH 2CH2CO2CH3 moieties in the β-pyrrolic positions and its use in the colorimetric detection of the uranyl cation after immobilization onto a solid supp
Porphyrins with Exocyclic Rings. Part 3. A Reassessment on the Utility of Cyclopentapyrroles in the Synthesis of Porphyrin Molecular Fossils. Preparation of Three Type II Porphyrins Related to Deoxophylloerythroetioporphyrin (DPEP)
Lash, Timothy D.,Catarello, James J.
, p. 4159 - 4172 (2007/10/02)
The utility of cyclopentapyrroles in porphyrin synthesis has been reinvestigated.A 6-oxocyclopentapyrrole 18 was prepared by cyclization of the propanoyl chloride sidechain of an α-unsubstituted pyrrole 17d in the presence of tin(IV) chloride.Subsequent reduction with sodium borohydride afforded the corresponding 6-hydroxy compound 10 and further acid catalyzed condensation with α-unsubstituted pyrroles 11a and 11b gave the novel 6-pyrrolylcyclopentapyrroles 22a and 22b in excellent yields.Attempts to prepare deoxophylloerythroetioporphyrin (DPEP; 2), a widespread sedimentary porphyrin molecular fossil, from these dipyrrolic intermediates using the tripyrrene-a,c-biladiene route were unsuccessful.However, the synthesis of three related meso,β-ethanoporphyrins using the MacDonald condensation was successfully carried out in moderate to good yields.Retention of an sp3 hybridized carbon bridge at the cyclopentene ring fusion site of the intermediary open chain tetrapyrroles appears to be crucial during macrocycle formation, as this diminishes the steric repulsion between the peripheral substituents and the carbocyclic ring.
Synthetic and Biosynthetic Studies of Porphyrins. Part 8. Synthese of Hepta-, Hexa-, and penta-carboxylic Porphyrins Related to Urophorphin-I
Jackson, Anthony H.,Supphayen, Damrus
, p. 277 - 286 (2007/10/02)
The title porphyrins of interest as abnormal metabolits in porphyrins biosynthesis, have been synthesized by the Fischer, and b-oxobilane routes, and compared with the naturally derived materials.Enzymic experiments have shown that the conversion of uropo
Biosynthesis of Porphyrins and Related Macrocycles. Part 25. Synthesis of Analogues of Coproporphyrinogen-III and Studies of their Interaction with Copropophyrinogen-III Oxidase from Euglena gracilis
Robinson, John A.,McDonald, Edward,Battersby, Alan R.
, p. 1699 - 1710 (2007/10/02)
Analogues of coproporphyrinogen-III have been synthesized in which the propionate groups respectively on ring-A and on ring-B are modified either by homologation or esterification.Coproporphyrinogen-III oxidase from Euglena gracilis acts on the analogues which possess normal substituents on ring-A to generate a vinyl group on that ring.The enzyme does not affect the analogues in which the ring-A propionate group has been changed.Conditions have been defined for the MacDonald synthesis of porphyrins which yield products of high isomeric purity.
