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Facile Synthesis of a "Ready to Use" Precursor of Porphobilinogen and Its Amino Acid Derivatives
Auteur(s)
Soldermann-Pissot, Carole
Vallinayagam, Ramakrishnan
Tzouros, Manuel
Date de parution
2008
In
J. Org. Chem.
Vol.
2
No
73
De la page
764
A la page
767
Mots-clés
- Amino acids Role: SPN (Synthetic preparation)
- PREP (Preparation) (conjugates
- prepn. of a precursor of porphobilinogen and its amino acid conjugates)
- Aldol condensation (crossed Mukayiama aldol reaction between silyl enol ethers and acyl cyanides)
- amino acid porphobilinogen precursor prepn crossed Mukayiama aldol reaction
Résumé
A practical synthesis of porphobilinogen based on the biosynthetic mechanism is described. The crossed Mukayiama aldol reaction is the key step creating the central carbon-carbon bond between the two protected forms of 5-aminolevulinic acids. The optimized sequence gives a cryst., storable precursor, which can be transformed in high yield into porphobilinogen and bioconjugates thereof. The enzymic hydrolysis of the precursor produces porphobilinogen in quant. yield. [on SciFinder(R)]
Identifiants
Type de publication
journal article
