2,3,4,6-Tetra-O-benzoyl-β-d-glucopyranosyl isothiocyanate: An efficient reagent for the determination of enantiomeric purities of amino acids, β-adrenergic blockers and alkyloxiranes by high-performance liquid chromatography using standard reversed-phase columns

Retention of the Cis Proline Conformation in Tripeptide Fragments of Bovine Pancreatic Ribonuclease A Containing a Non-natural Proline Analogue, 5,5-Dimethylproline

“…The absolute configuration of the isomer of dmP forming the insoluble crystalline complex with d-tartaric acid was identified as l by 1 H NMR spectroscopy of the methyl ester of the dmP isomer in ( R )-(−)-1-phenyl-2,2,2-trifluoroethanol . The purity of the l -dmP (>98%; mp 193.5 °C) was determined by using 2,3,4,6-tetra- O -benzyl-β- d -glucopyranosyl isothiocyanate (BGIT), which can form diastereomeric thioureas with d , l -dmP without racemization . The diastereomers can be separated on a nonchiral reversed-phase (RP) C-18 column (Vydac C-18, 4.6 × 100) by high-pressure liquid chromatography (HPLC), using as a mobile phase 10 mM phosphate, pH 7, 60−70% MeOH gradient.…”

Chiral derivatization reagents for drug enantioseparation by high‐performance liquid chromatography based upon pre‐column derivatization and formation of diastereomers: enantioselectivity and related structure

“…In addition, more acceptable asymmetry of the chromatography was also achieved (Olsen et al, 1993). Lobell and Schneider (1993) investigated the influence of more bulky groups (benzoyl, acetyl and pivaloyl) introduced into saccharide molecules, which were used as the candidate chiral derivatization reagents for enantioseparation of amino alcohols or amino acids, on the resolution of the diastereomeric thioureas on a reveredphase column. Good resolutions of diastereomeric thiourea derivatives formed by derivatization of 17 racemic amino acids and six racemic b-adrenergic blockers with BGIT were obtained.…”

Synthesis of new stable aliphatic isothiocyanate-based chiral derivatizing agent and application to indirect separation of chiral amino and thiol compounds

“…As with any isothiocyanate [3,4,25,29], (S,S)-PDITC reacts selectively in aqueous or non-aqueous media with chiral primary and secondary amino functions of amines, amino alcohols, amino acids and peptides forming the corresponding diastereomeric thioureas. Another functionality which can be derivatized by isothio- Derivatization scheme of amino-and thiol-compounds using (S,S)-PDITC as CDA cyanates is the thiol group [29,35] which leads to the corresponding dithiocarbamates.…”

“…At chosen chromatographic conditions (see experimental) detection limits in the low nM range are obtainable. The thiocarbonyl groups of GITC derived leucine had a molar extinction coefficient of 9.500 at 250 nm [4].…”

“…The most widely reported CDAs to derivatise amino compounds are 2,3,4,6-tetra-O-acetyl-[3-D-glucopyranosyl isothiocyanate (GITC) [3,14,23], 2,3,4-tri-Oacetyl-ct-D-arabinopyranosyl isothiocyanate (AITC) [3], 2,3,4,6-tetra-O-benzoyl-13-D-gtucopyranosyI isothiocyanate (BGIT) [4] and N-(5-fluoro-2,4-dinitrophenyl)-L-alanine amide (Marfey's reagent) [24]. The following CDAs 4-(3-isothiocyanato-2-pyrrolidin-l-yl)-7-nitro-2,1,3-benzoxadiazole (NBD-PyNCS) [25] and 4-(3-isothiocyanato-pyrrolidin-l-yl)-7-(N,N-dimethylaminosulfonyl)-2,1,3-benzoxadiazole (DBD-PyNCS) [26] belong to a group of fluorescence-active, chiral tagging reagents.…”