Theoretical study of 5-aminolevulinic acid tautomerization: a novel self-catalyzed mechanism

The Journal of Physical Chemistry. a
Edvin Erdtman, Leif A Eriksson

Abstract

5-Aminolevulinic acid (5ALA) is the key synthetic building block in protoporphyrin IX (PpIX), the heme chromophore in mitochondria. In this study density functional theory calculations were performed on the tautomers of 5ALA and the tautomerization reaction mechanism from its enolic forms (5-amino-4-hydroxypent-3-enoic acid and 5-amino-4-hydroxypent-4-enoic acid) to the more stable 5ALA. The hydrated form 5-amino-4,4-dihydroxypentanoic acid was also studied. The lowest energy pathway of 5ALA tautomerization is by means of autocatalysis, in that an oxygen of the carboxylic group transfers the hydrogen atom as a "crane", with an activation energy of approximately 15 kcal/mol. This should be compared to the barriers of about 35 kcal/mol for water assisted tautomerization, and 60 kcal/mol for direct hydrogen transfer. For hydration of 5ALA, the water catalyzed activation barrier is found to be approximately 35 kcal/mol, approximately 5 kcal/mol lower than direct hydration.

References

Sep 12, 2000·Journal of Pharmaceutical Sciences·A BunkeB Gander
May 30, 1953·Nature·J D WATSON, F H CRICK
Feb 15, 2007·The Journal of Physical Chemistry. a·Mark A FreitagMarcel Fallet

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Citations

Apr 9, 2011·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Yan-Fang LiuRuo-Zhuang Liu

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