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Theoretical Study of the o-OH Participation in Catechol Ester Ammonolysis

Theoretical Study of the o-OH Participation in Catechol Ester Ammonolysis

Miroslav A Rangelov, Georgi N Vayssilov, Vihra M Yomtova, Dimiter D Petkov

Org Biomol Chem. 2005 Mar 7;3(5):737-44.

PMID: 15731858

Abstract:

The possible catalytic effect of the vicinal hydroxyl group during the ammonolysis of acetylcatechol has been studied by first principle calculations. A very efficient intramolecular catalysis was found to occur when the catechol ester o-OH group is deprotonated: the activation energy of the ammonolysis decreases by 24 kcal mol(-1) as compared to that of acetylphenol ammonolysis. Using this value, the o-oxyanion-catalysed intramolecular ammonolysis was estimated to be orders of magnitude faster than the ammonolysis of acetylphenol or nonionised acetylcatechol. The analogy with the aminolysis of peptidyl-tRNA that occurs during protein biosynthesis implies several orders of magnitude acceleration due to complete or partial deprotonation of its 3'-terminal adenosine 2'-OH providing a mechanistic possibility for general acid-base catalysis by the ribosome.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP142172518	4-Bromo-1-butylboronic acid catechol ester		142172-51-8	Price

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