Glycopyrronium Bromide EP Impurity C (S-Isomer)
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| Category | Others |
| Catalog number | BBF-04751 |
| CAS | 17199-29-0 |
| Molecular Weight | 152.15 |
| Molecular Formula | C8H8O3 |
| Purity | ≥ 99 % |
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Description
An impurity of Glycopyrrolate, which is an anticholinergic agent with antispasmodic activity used to treat gastrointestinal conditions associated.
Specification
| Synonyms | (S)-(+)-Mandelic acid; (S)-Mandelic acid; L-mandelic acid |
| Storage | Keep in dark place. Room temperature. |
| IUPAC Name | (2S)-2-hydroxy-2-phenylacetic acid |
| Canonical SMILES | C1=CC=C(C=C1)C(C(=O)O)O |
| InChI | InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1 |
| InChI Key | IWYDHOAUDWTVEP-ZETCQYMHSA-N |
Properties
| Appearance | Powder or crystals |
| Boiling Point | 321.8 ℃ / 760 mmHg |
| Melting Point | 131-134 ℃ |
| Flash Point | > 190 °C(374.0 °F) |
| Density | 1.321 g/cm3 |
| Solubility | Soluble in water. |
| LogP | 0.80460 |
Reference Reading
1. Investigating chiral recognizability of diastereomeric crystallization of mandelic acid and l-phenylalanine.
Sang Mok Chang, Xuan-Hung Pham, Jong Min Kim, In Ho Kim, Woo-Sik Kim. J Nanosci Nanotechnol. 2012 Sep; 12(9): 7139-47. DOI: 10.1166/jnn.2012.6490. PMID: 23035445.
The present study investigated the mechanism of the chiral recognition of the resolving agent (L-phenylalanine) to the chiral isomers (D/L-mandelic acid). According the NMR analysis, the distinctive chemical shifts of between two diastereomer crystals (L-mandelic acid-L-phenlyalanine and D-mandelic acid-L-phenylalanine) were observed even though there was no difference of the chemicals shift of the two diastereomer solutions. This result indicated that the chiral recognition of the resolving agent mainly occurred during the crystallization of the diastereomers in the solution. Then, the chiral recognition of the diastereomers was confirmed by using thermal analysis and AFM. The diastereomer crystal of L-mandelic acid-L-phenylalanine was much more thermally stable due to the higher lattice energy than the diastereomer crystals of D-mamdelic acid-L-phenylalanine. Also, the adhesive force measured with AFM exhibited a stronger molecular interaction between L-mandelic acid and 4-amino-L-phenylalanine than between D-mandelic acid and 4-amino-L-phenylalanine. Plus, the AFM results implied that the hydroxyl group abundance on the mandelic acid surface was a possible explanation for the different chiral selectivity of the L-phenylalanine.
2. A double mutant of highly purified geobacillus stearothermophilus lactate dehydrogenase recognises l-mandelic acid as a substrate.
Barış Binay, Nevin Gül Karagüler, Richard B Sessions. Enzyme Microb Technol. 2013 May 10; 52(6-7): 393-9. DOI: 10.1016/j.enzmictec.2013.01.009. PMID: 23608509.
Lactate dehydrogenase from the thermophilic organism Geobacillus stearothermophilus (formerly Bacillus stearothermophilus) (bsLDH) has a crucial role in producing chirally pure hydroxyl compounds. α-Hydroxy acids are used in many industrial situations, ranging from pharmaceutical to cosmetic dermatology products. One drawback of this enzyme is its limited substrate specificity. For instance, l-lactate dehydrogenase exhibits no detectable activity towards the large side chain of 2-hydroxy acid l-mandelic acid, an α-hydroxy acid with anti-bacterial activity. Despite many attempts to engineer bsLDH to accept α-hydroxy acid substrates, there have been no attempts to introduce the industrially important l-mandelic acid to bsLDH. Herein, we describe attempts to change the reactivity of bsLDH towards l-mandelic acid. Using the Insight II molecular modelling programme (except 'program' in computers) and protein engineering techniques, we have successfully introduced substantial mandelate dehydrogenase activity to the enzyme. Energy minimisation modelling studies suggested that two mutations, T246G and I240A, would allow the enzyme to utilise l-mandelic acid as a substrate. Genes encoding for the wild-type and mutant enzymes were constructed, and the resulting bsLDH proteins were overexpressed in Escherichia coli and purified using the TAGZyme system. Enzyme assays showed that insertion of this double mutation into highly purified bsLDH switched the substrate specificity from lactate to l-mandelic acid.
3. Chiral separation of d,L-mandelic acid through cellulose membranes.
Hai-Qin Shan, Sheng-Ming Xie, Ping Ai, Ying-Chun Lv, Chao Ma, Xiao-Lin Xu, Li-Ming Yuan. Chirality. 2011 May; 23(5): 379-82. DOI: 10.1002/chir.20935. PMID: 21488105.
This work reports the chiral separation of D,L-mandelic acid with cellulose membranes. Cellulose was chosen as membrane material because it possesses multichiral carbon atoms in its molecular structure unit. The flux and permselective properties of membrane using aqueous solutions of D,L-mandelic acid as feed solution was studied. The top surface and cross-section morphology of the resulting membrane were examined by scanning electron microscopy. When the membrane was prepared with 8.1 wt % cellulose and 8.1 wt % LiCl in the DMA casting solution, and the operating pressure and feed concentration of racemate were 0.0125 MPa and 0.5 mg/ml, respectively, over 90% of enantiomeric excess could be obtained. This is the first report that the cellulose membrane is used for isolating the optical isomers of D,L-mandelic acid. Chirality, 2011.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
