Highly stereospecific epimerization of α-amino acids: Conducted tour mechanism

Indrajit Bandyopadhyay, Han Myoung Lee, P. Tarakeshwar, Chunzhi Cui, Kyong Seok Oh, Jik Chin, Kwang S. Kim

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

The highly stereospecific and regiospecific recognition of α-amino acids exhibited by a novel Co(III) metal complex embodied in the experimental work (Nature 1999, 401, 254) is rationalized from the energetics and structural characteristics with the use of density functional calculations. The steric repulsion between the chiral center of the receptor [Co(III) complex] and alanine has been a cause for the discrimination of complex stabilities. The energies evaluated for all possible alanine binding modes clearly reveal regiospecificity. Our main emphasis is laid on the base-catalyzed epimerization reaction that drives the stereospecific recognition to near completion. The conducted tour mechanism is found to be the most likely candidate. A similar role by the equivalent Zn(II) complex is found.

Original languageEnglish (US)
Pages (from-to)6571-6575
Number of pages5
JournalJournal of Organic Chemistry
Volume68
Issue number17
DOIs
StatePublished - Sep 1 2003
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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    Bandyopadhyay, I., Lee, H. M., Tarakeshwar, P., Cui, C., Oh, K. S., Chin, J., & Kim, K. S. (2003). Highly stereospecific epimerization of α-amino acids: Conducted tour mechanism. Journal of Organic Chemistry, 68(17), 6571-6575. https://doi.org/10.1021/jo034130c