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

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

Research output: Contribution to journalArticle

7 Citations (Scopus)

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

Fingerprint

Alanine
Amino Acids
Coordination Complexes
Density functional theory

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Bandyopadhyay, I., Lee, H. M., Pilarisetty, T., 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

Highly stereospecific epimerization of α-amino acids : Conducted tour mechanism. / Bandyopadhyay, Indrajit; Lee, Han Myoung; Pilarisetty, Tarakeshwar; Cui, Chunzhi; Oh, Kyong Seok; Chin, Jik; Kim, Kwang S.

In: Journal of Organic Chemistry, Vol. 68, No. 17, 01.09.2003, p. 6571-6575.

Research output: Contribution to journalArticle

Bandyopadhyay, I, Lee, HM, Pilarisetty, T, Cui, C, Oh, KS, Chin, J & Kim, KS 2003, 'Highly stereospecific epimerization of α-amino acids: Conducted tour mechanism', Journal of Organic Chemistry, vol. 68, no. 17, pp. 6571-6575. https://doi.org/10.1021/jo034130c
Bandyopadhyay, Indrajit ; Lee, Han Myoung ; Pilarisetty, Tarakeshwar ; Cui, Chunzhi ; Oh, Kyong Seok ; Chin, Jik ; Kim, Kwang S. / Highly stereospecific epimerization of α-amino acids : Conducted tour mechanism. In: Journal of Organic Chemistry. 2003 ; Vol. 68, No. 17. pp. 6571-6575.
@article{ba0364b4d21948a29457a6cd55600eef,
title = "Highly stereospecific epimerization of α-amino acids: Conducted tour mechanism",
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.",
author = "Indrajit Bandyopadhyay and Lee, {Han Myoung} and Tarakeshwar Pilarisetty and Chunzhi Cui and Oh, {Kyong Seok} and Jik Chin and Kim, {Kwang S.}",
year = "2003",
month = "9",
day = "1",
doi = "10.1021/jo034130c",
language = "English (US)",
volume = "68",
pages = "6571--6575",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "17",

}

TY - JOUR

T1 - Highly stereospecific epimerization of α-amino acids

T2 - Conducted tour mechanism

AU - Bandyopadhyay, Indrajit

AU - Lee, Han Myoung

AU - Pilarisetty, Tarakeshwar

AU - Cui, Chunzhi

AU - Oh, Kyong Seok

AU - Chin, Jik

AU - Kim, Kwang S.

PY - 2003/9/1

Y1 - 2003/9/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0042510134&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0042510134&partnerID=8YFLogxK

U2 - 10.1021/jo034130c

DO - 10.1021/jo034130c

M3 - Article

C2 - 12919017

AN - SCOPUS:0042510134

VL - 68

SP - 6571

EP - 6575

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 17

ER -