A mass spectrometry method for the determination of enantiomeric excess in mixtures of D,L-amino acids

Gabriela Grigorean, Javier Ramirez, Seong He Ahn, Carlito B Lebrilla

Research output: Contribution to journalArticle

103 Citations (Scopus)

Abstract

A mass spectrometry method based on ion/molecule reactions for determining enantiomeric excess in mixtures of amino acids is illustrated. Protonated complexes of amino acids with β-cyclodextrin are produced in the gas phase using electrospray ionization. Under a background pressure of N-propylamine, the amino acid is replaced by the alkylamine. The rates of the guest exchange reaction vary with the chirality of the amino acid. A calibration curve employing varying mixtures of D- and L-amino acids is produced and the fractions of the D isomer in the test mixtures are determined. The quality of the curve is compared to the chiral selectivity of the reaction. In general, the best calibration curves are obtained in systems with the greatest selectivity.

Original languageEnglish (US)
Pages (from-to)4275-4281
Number of pages7
JournalAnalytical Chemistry
Volume72
Issue number18
StatePublished - Sep 15 2000

Fingerprint

Mass spectrometry
Amino Acids
Propylamines
Calibration
Electrospray ionization
Chirality
Cyclodextrins
Isomers
Gases
Ions
Molecules

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

Grigorean, G., Ramirez, J., Ahn, S. H., & Lebrilla, C. B. (2000). A mass spectrometry method for the determination of enantiomeric excess in mixtures of D,L-amino acids. Analytical Chemistry, 72(18), 4275-4281.

A mass spectrometry method for the determination of enantiomeric excess in mixtures of D,L-amino acids. / Grigorean, Gabriela; Ramirez, Javier; Ahn, Seong He; Lebrilla, Carlito B.

In: Analytical Chemistry, Vol. 72, No. 18, 15.09.2000, p. 4275-4281.

Research output: Contribution to journalArticle

Grigorean, G, Ramirez, J, Ahn, SH & Lebrilla, CB 2000, 'A mass spectrometry method for the determination of enantiomeric excess in mixtures of D,L-amino acids', Analytical Chemistry, vol. 72, no. 18, pp. 4275-4281.
Grigorean, Gabriela ; Ramirez, Javier ; Ahn, Seong He ; Lebrilla, Carlito B. / A mass spectrometry method for the determination of enantiomeric excess in mixtures of D,L-amino acids. In: Analytical Chemistry. 2000 ; Vol. 72, No. 18. pp. 4275-4281.
@article{fa955c2458394caa8b505884145ab582,
title = "A mass spectrometry method for the determination of enantiomeric excess in mixtures of D,L-amino acids",
abstract = "A mass spectrometry method based on ion/molecule reactions for determining enantiomeric excess in mixtures of amino acids is illustrated. Protonated complexes of amino acids with β-cyclodextrin are produced in the gas phase using electrospray ionization. Under a background pressure of N-propylamine, the amino acid is replaced by the alkylamine. The rates of the guest exchange reaction vary with the chirality of the amino acid. A calibration curve employing varying mixtures of D- and L-amino acids is produced and the fractions of the D isomer in the test mixtures are determined. The quality of the curve is compared to the chiral selectivity of the reaction. In general, the best calibration curves are obtained in systems with the greatest selectivity.",
author = "Gabriela Grigorean and Javier Ramirez and Ahn, {Seong He} and Lebrilla, {Carlito B}",
year = "2000",
month = "9",
day = "15",
language = "English (US)",
volume = "72",
pages = "4275--4281",
journal = "Analytical Chemistry",
issn = "0003-2700",
publisher = "American Chemical Society",
number = "18",

}

TY - JOUR

T1 - A mass spectrometry method for the determination of enantiomeric excess in mixtures of D,L-amino acids

AU - Grigorean, Gabriela

AU - Ramirez, Javier

AU - Ahn, Seong He

AU - Lebrilla, Carlito B

PY - 2000/9/15

Y1 - 2000/9/15

N2 - A mass spectrometry method based on ion/molecule reactions for determining enantiomeric excess in mixtures of amino acids is illustrated. Protonated complexes of amino acids with β-cyclodextrin are produced in the gas phase using electrospray ionization. Under a background pressure of N-propylamine, the amino acid is replaced by the alkylamine. The rates of the guest exchange reaction vary with the chirality of the amino acid. A calibration curve employing varying mixtures of D- and L-amino acids is produced and the fractions of the D isomer in the test mixtures are determined. The quality of the curve is compared to the chiral selectivity of the reaction. In general, the best calibration curves are obtained in systems with the greatest selectivity.

AB - A mass spectrometry method based on ion/molecule reactions for determining enantiomeric excess in mixtures of amino acids is illustrated. Protonated complexes of amino acids with β-cyclodextrin are produced in the gas phase using electrospray ionization. Under a background pressure of N-propylamine, the amino acid is replaced by the alkylamine. The rates of the guest exchange reaction vary with the chirality of the amino acid. A calibration curve employing varying mixtures of D- and L-amino acids is produced and the fractions of the D isomer in the test mixtures are determined. The quality of the curve is compared to the chiral selectivity of the reaction. In general, the best calibration curves are obtained in systems with the greatest selectivity.

UR - http://www.scopus.com/inward/record.url?scp=0034665682&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034665682&partnerID=8YFLogxK

M3 - Article

VL - 72

SP - 4275

EP - 4281

JO - Analytical Chemistry

JF - Analytical Chemistry

SN - 0003-2700

IS - 18

ER -