An insight to the cleavage of Β-carotene to vitamin A: a molecular mechanics study

Mohamed, N. and Zain, Sharifuddin Md and Rahman, N.A. and Hashim, R. (2001) An insight to the cleavage of Β-carotene to vitamin A: a molecular mechanics study. Journal of Molecular Structure: THEOCHEM, 538. pp. 245-252. ISSN 01661280

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Abstract

The conversion mechanism of β-carotene to vitamin A has been a topic of much discussion for many years since the first proposal of central cleavage mechanism, which was soon challenged by arguments supporting the eccentric cleavage mechanism. Inconclusive evidences have led to the proposal that the conversion of β-carotene does take place through both these mechanisms, possibly by different oxygenase enzymes at different locations in the body. In order to have further insight and better understanding of the cleavage mechanism, molecular mechanics calculations were performed on several cis- and trans-conformations of β-carotene at different polyene portion. The results indicated a series of relatively low energy cis-conformers in addition to the all trans-conformer with lowest energy conformation being the cis-C9′-C10′ double bond (E = 46.46 kcal/mol in water) which could act as the possible starting conformer for the reaction. The molecular mechanics (MM) energy of various cyclic peroxide structures was also carried out and the results seem to support the formation of vitamin A via a systematic degradation of β-carotene. © 2001 Elsevier Science B.V.

Item Type: Article
Additional Information: Department of Chemistry, Faculty of Science Building, University of Malaya, 50603 Kuala Lumpur, MALAYSIA
Uncontrolled Keywords: β-Carotene, Cyclic peroxide, Molecular modeling, beta carotene, carotenoid, peroxide, retinol, article, chemical reaction, energy, geometry, molecular model, vitamin metabolism, X ray crystallography
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Dept of Chemistry
Depositing User: Miss Malisa Diana
Date Deposited: 19 Apr 2013 01:00
Last Modified: 24 Jan 2019 09:08
URI: http://eprints.um.edu.my/id/eprint/5841

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