Evaluation of (R)-(−)-α-methoxy phenyl acetic acid as a chiral shift reagent for resolution and determination of R and S enantiomers of modafinil in bulk drugs and formulations by 1H NMR spectroscopy

Ramisetti Nageswara Rao; Bondigalla Ramachandra; Kondapalli Santhakumar

doi:10.1002/chir.22002

Evaluation of (R)-(−)-α-methoxy phenyl acetic acid as a chiral shift reagent for resolution and determination of R and S enantiomers of modafinil in bulk drugs and formulations by 1H NMR spectroscopy

Chirality ◽

10.1002/chir.22002 ◽

2012 ◽

Vol 24 (4) ◽

pp. 339-344 ◽

Cited By ~ 6

Author(s):

Ramisetti Nageswara Rao ◽

Bondigalla Ramachandra ◽

Kondapalli Santhakumar

Keyword(s):

Acetic Acid ◽

Nmr Spectroscopy ◽

1H Nmr ◽

1H Nmr Spectroscopy ◽

Shift Reagent ◽

Phenyl Acetic Acid ◽

Chiral Shift Reagent

Use of shift reagent with MTPA derivatives in 1H NMR spectroscopy. III. Determination of absolute configuration and enantiomeric purity of primary carbinols with chiral center at the C-2 position

Tetrahedron Letters ◽

10.1016/s0040-4039(01)83433-x ◽

1977 ◽

Vol 18 (47) ◽

pp. 4085-4088 ◽

Cited By ~ 21

Author(s):

Fujiko Yasuhara ◽

Shozo Yamaguchi

Keyword(s):

Nmr Spectroscopy ◽

1H Nmr ◽

Absolute Configuration ◽

1H Nmr Spectroscopy ◽

Shift Reagent ◽

Enantiomeric Purity ◽

Chiral Center ◽

Determination Of Absolute Configuration

Determination of absolute configuration of the derivative from 2-[4-(1-oxo-2-isoindolinyl)-phenyl]-propionic acid and R-(+)-1-phenylethylamine by 1H-NMR spectroscopy; use of shift reagent with diastereoisomeric amides

Tetrahedron Letters ◽

10.1016/0040-4039(80)80022-0 ◽

1980 ◽

Vol 21 (23) ◽

pp. 2273-2276 ◽

Cited By ~ 11

Author(s):

Sergio De Munari ◽

Giuseppe Marazzi ◽

Angelo Forgione ◽

Antonio Longo ◽

Paolo Lombardi

Keyword(s):

Nmr Spectroscopy ◽

Propionic Acid ◽

1H Nmr ◽

Absolute Configuration ◽

1H Nmr Spectroscopy ◽

Shift Reagent ◽

Phenyl Propionic Acid ◽

Determination Of Absolute Configuration

Use of shift reagent with MTPA derivatives in 1H NMR spectroscopy. II. determination of absolute configuration and diastereomeric composition of secondary carbinols in epimeric mixture

Tetrahedron Letters ◽

10.1016/s0040-4039(01)92558-4 ◽

1977 ◽

Vol 18 (1) ◽

pp. 89-92 ◽

Cited By ~ 16

Author(s):

Shozo Yamaguchi ◽

Fujiko Yasuhara

Keyword(s):

Nmr Spectroscopy ◽

1H Nmr ◽

Absolute Configuration ◽

1H Nmr Spectroscopy ◽

Shift Reagent ◽

Determination Of Absolute Configuration

Use of shift reagent with MTPA derivatives in 1H NMR spectroscopy. IV. Determination of absolute configuration and enantiomeric purity of amino acid derivatives.

Tetrahedron Letters ◽

10.1016/s0040-4039(01)95204-9 ◽

1978 ◽

Vol 19 (44) ◽

pp. 4289-4292 ◽

Cited By ~ 9

Author(s):

Fujiko Yasuhara ◽

Kuninobu Kabuto ◽

Shozo Yamaguchi

Keyword(s):

Amino Acid ◽

Nmr Spectroscopy ◽

1H Nmr ◽

Absolute Configuration ◽

1H Nmr Spectroscopy ◽

Shift Reagent ◽

Enantiomeric Purity ◽

Amino Acid Derivatives ◽

Determination Of Absolute Configuration

Determination of compositional sequences in PCT/FT aromatic copolyterephthalate by 1H-NMR spectroscopy and Pr(fod)3 lanthanide shift reagent

Polymer Bulletin ◽

10.1007/bf00255334 ◽

1987 ◽

Vol 18 (6) ◽

Author(s):

Marek Matlengiewicz

Keyword(s):

Nmr Spectroscopy ◽

1H Nmr ◽

1H Nmr Spectroscopy ◽

Shift Reagent ◽

Lanthanide Shift Reagent

Use of shift reagent with diastereomeric MTPA esters for determination of configuration and enantiomeric purity of secondary carbinols in 1H NMR spectroscopy

Tetrahedron ◽

10.1016/0040-4020(76)85011-9 ◽

1976 ◽

Vol 32 (12) ◽

pp. 1363-1367 ◽

Cited By ~ 63

Author(s):

Shozo Yamaguchi ◽

Fujiko Yasuhara ◽

Kuninobu Kabuto

Keyword(s):

Nmr Spectroscopy ◽

1H Nmr ◽

1H Nmr Spectroscopy ◽

Shift Reagent ◽

Enantiomeric Purity

Primary structure determination of five sialylated oligosaccharides derived from bronchial mucus glycoproteins of patients suffering from cystic fibrosis. The occurrence of the NeuAc alpha(2----3)Gal beta(1----4)[Fuc alpha(1----3)] GlcNAc beta(1----.) structural element revealed by 500-MHz 1H NMR spectroscopy.

Journal of Biological Chemistry ◽

10.1016/s0021-9258(17)47263-2 ◽

1984 ◽

Vol 259 (14) ◽

pp. 9051-9058 ◽

Cited By ~ 13

Author(s):

G Lamblin ◽

A Boersma ◽

A Klein ◽

P Roussel ◽

H van Halbeek ◽

...

Keyword(s):

Cystic Fibrosis ◽

Nmr Spectroscopy ◽

1H Nmr ◽

Structure Determination ◽

Primary Structure ◽

1H Nmr Spectroscopy ◽

Structural Element ◽

Bronchial Mucus ◽

Mucus Glycoproteins

Highly Functionalised Cyclopentanes by Radical Cyclisation of Unsaturated Bromolactones III. Preparation of Carbaaldohexofuranoses. Determination of the Relative Configuration at C-4/C-5 of 2,3-Unsaturated Heptono-1,4-lactones by Means of 1H NMR Spectroscopy

Synthesis ◽

10.1055/s-1999-3384 ◽

1999 ◽

Vol 1999 (02) ◽

pp. 317-325 ◽

Cited By ~ 10

Author(s):

Anne Marie Horneman ◽

Inge Lundt

Keyword(s):

Nmr Spectroscopy ◽

1H Nmr ◽

1H Nmr Spectroscopy ◽

Relative Configuration

pKa Determination of a Histidine Residue in a Short Peptide Using Raman Spectroscopy

Molecules ◽

10.3390/molecules24030405 ◽

2019 ◽

Vol 24 (3) ◽

pp. 405 ◽

Cited By ~ 6

Author(s):

Brett H. Pogostin ◽

Anders Malmendal ◽

Casey H. Londergan ◽

Karin S. Åkerfeldt

Keyword(s):

Raman Spectroscopy ◽

Nmr Spectroscopy ◽

1H Nmr ◽

1H Nmr Spectroscopy ◽

Peptide Sequence ◽

Short Peptide ◽

Dependent Behavior ◽

Pka Determination ◽

Key Functional Groups

Determining the pKa of key functional groups is critical to understanding the pH-dependent behavior of biological proteins and peptide-based biomaterials. Traditionally, 1H NMR spectroscopy has been used to determine the pKa of amino acids; however, for larger molecules and aggregating systems, this method can be practically impossible. Previous studies concluded that the C-D stretches in Raman are a useful alternative for determining the pKa of histidine residues. In this study, we report on the Raman application of the C2-D probe on histidine’s imidazole side chain to determining the pKa of histidine in a short peptide sequence. The pKa of the tripeptide was found via difference Raman spectroscopy to be 6.82, and this value was independently confirmed via 1H NMR spectroscopy on the same peptide. The C2-D probe was also compared to other Raman reporters of the protonation state of histidine and was determined to be more sensitive and reliable than other protonation-dependent signals. The C2-D Raman probe expands the tool box available to chemists interested in directly interrogating the pKa’s of histidine-containing peptide and protein systems.

1H NMR Spectroscopy for Determination of the Geographical Origin of Hazelnuts

Journal of Agricultural and Food Chemistry ◽

10.1021/acs.jafc.8b03724 ◽

2018 ◽

Vol 66 (44) ◽

pp. 11873-11879 ◽

Cited By ~ 16

Author(s):

René Bachmann ◽

Sven Klockmann ◽

Johanna Haerdter ◽

Markus Fischer ◽

Thomas Hackl

Keyword(s):

Nmr Spectroscopy ◽

1H Nmr ◽

1H Nmr Spectroscopy ◽

Geographical Origin