Improved discrimination of phenylalanine enantiomers by surface enhanced Raman scattering assay: molecular insight into chiral interaction

Abstract

SERS spectroscopy, a nontraditional chiral analysis tool, is used to discriminate D- and L- phenylalanine (Phe), with the Raman scattering enhancement degree of D-Phe is 50-fold greater than L-Phe. Such...

Enantioselective and Chemoselective Optical Detection of Chiral Organic Compounds without Resorting to Chromatography

“…The characteristic vibrational mode of quinine with the corresponding aliphatic amino acid resulted into a unique SERS spectrum for each amino acid and a significant difference in the area ratio of the bands at 1362 and 1380 cm −1 was found between D‐ and L‐enantiomers for each case. It is already established that tremendous enhancement in SERS is provided by the high intensity of the localized field in the plasmonic nanogaps (especially in the sub‐nanometer range). Allowing chiral interactions between Phe and the chiral drug molecule of sertraline (a selective serotonin reuptake inhibitor pharmaceutically more useful as ( S , S )‐isomer) on silver coated gold nanorods (Au@Ag NR), He et al ., applied SERS to discriminate between D‐ and L‐Phe [105] . Sertraline acted as an enantiomer‐selective amplifier to improve SERS discrimination of enantiomers and its SERS signals were not recorded on Au@Ag NR substrates.…”

“…Allowing chiral interactions between Phe and the chiral drug molecule of sertraline (a selective serotonin reuptake inhibitor pharmaceutically more useful as ( S , S )‐isomer) on silver coated gold nanorods (Au@Ag NR), He et al ., applied SERS to discriminate between D‐ and L‐Phe [105] . Sertraline acted as an enantiomer‐selective amplifier to improve SERS discrimination of enantiomers and its SERS signals were not recorded on Au@Ag NR substrates.…”

“…(v) Allowing chiral interactions between Phe and the chiral drug molecule of sertraline (a selective serotonin reuptake inhibitor pharmaceutically more useful as (S,S)-isomer) on silver coated gold nanorods (Au@Ag NR), He et al, applied SERS to discriminate between D-and L-Phe. [105] Sertraline acted as an enantiomer-selective amplifier to improve SERS discrimination of enantiomers and its SERS signals were not recorded on Au@Ag NR substrates. The experiments reported showed that the SERS intensity enhancement degree of D-Phe was 50-fold greater than that of L-Phe when sertraline was mixed with Au@AgÀ DÀ Phe or Au@AgÀ LÀ Phe, and there were no experiments on mixtures of the two enantiomers of different ee.…”

Coupling of plasmonic hot spots with shurikens for superchiral SERS-based enantiomer recognition

“…24–26 Additionally, plasmon-active structures were functionalized with secondary probe molecules to mediate stereospecific analyte–probe interactions or ensure selective entrapping of enantiomers near plasmon active surface for subsequent SERS measurements. 27–30…”

“…[24][25][26] Additionally, plasmonactive structures were functionalized with secondary probe molecules to mediate stereospecific analyte-probe interactions or ensure selective entrapping of enantiomers near plasmon active surface for subsequent SERS measurements. [27][28][29][30] On other hand, the significant progress in the field of nanomaterials construction and preparation led to gradual appearance of structures, able to support the excitation of intrinsically chiral plasmons. 9,[31][32][33][34] Recent research indicate that such structures are promising candidate for SERS based enantiomeric discrimination.…”