Numerous methods are utilized to synthesize porphyrins, depending on the target porphyrin structure and symmetry; selection of porphyrin building blocks are key for an efficient successful synthesis. The condensation of pyrroles with aldehydes and subsequent oxidation is the most widely used methodology for porphyrin synthesis. Substitution resulting from this methodology is limited to symmetric porphyrins due to the use of identically substituted pyrroles. Several other approaches are also used to synthesize complex asymmetrically substituted porphyrins. These methodologies include the 2+2 MacDonald cyclization and Fischer porphyrin synthesis which proceed by the condensation of two dipyrrolemethene building blocks. Condensation of an α-tripyrrole with a 2,5-diformylpyrrole using a 3+1 approach and cyclization of open chain tetrapyrroles such as b-bilenes and a,c-biladienes can also be used to synthesize highly functionalized asymmetric porphyrins.
Many highly functionalized porphyrinoid compounds can be synthesized by synthetic modification of natural porphyrin derivatives such as chlorophyll and heme.
Frontier Specialty Chemicals offers numerous building blocks for the synthesis of novel porphyrins and related compounds.
Substituted pyrrole building blocks available from Frontier Scientific
Specific synthetic examples using substituted pyrroles available from Frontier Scientific
Catalog Number: E15129
Ivanova, Y.B., Mamardashvili, N.Z., Glazunov, A.V. et al, Russ J Gen Chem. 85, 640–647, 2015
Catalog Number: P12623
Guilard, R. et al, Synthesis, (12), 1480-2; 1995
Catalog Number: T1927
Sugiura, Ken-ichi et al, Journal of Materials Chemistry, 10 (11), 2507-2514; 2000
Dipyrromethanes
| Catalog Number: PB12171 | Catalog Number: PB12760 | Catalog Number: PB13620 | Catalog Number: PB1978 | Catalog Number: PB1979 |
Specific Synthetic examples of the use of dipyrromethanes in porphyrin synthesis
Catalog Number: PB12171
Malatesti, Nela et al, International Journal of Oncology, 28 (6), 1561-1569; 2006
Catalog Number: PB1988
Nagpal, Ritika et al, ChemistrySelect, 4 (29), 8444-8449; 2019
Tetrapyrroles
Porphyrins which are asymmetric and have a different substituents at the β positions can be synthesized using cyclization of open chain tetrapyrroles. Oxidative cyclization of linear tetrapyrroles using transition metals gives the desired porphyrin.
| Catalog Number: M14136 Mesobiliverdin | Catalog Number: P14137 Phycocyanobilin | Catalog Number: B610-9 Biliverdin Dimethyl Ester |