N-Methyl-D-proline
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| Category | Others |
| Catalog number | BBF-05240 |
| CAS | 58123-62-9 |
| Molecular Weight | 129.16 |
| Molecular Formula | C6H11NO2 |
| Purity | ≥95% by HPLC |
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Specification
| Related CAS | 1217447-61-4 (hydrate) 702710-17-6 (hydrochloride) |
| Synonyms | N-Me-D-Pro-OH; 1-methyl-D-Proline; (R)-1-methylpyrrolidine-2-carboxylic acid; methyl-D-proline |
| Storage | Store at -20°C |
| IUPAC Name | (2R)-1-methylpyrrolidine-2-carboxylic acid |
| Canonical SMILES | CN1CCCC1C(=O)O |
| InChI | InChI=1S/C6H11NO2/c1-7-4-2-3-5(7)6(8)9/h5H,2-4H2,1H3,(H,8,9)/t5-/m1/s1 |
| InChI Key | CWLQUGTUXBXTLF-RXMQYKEDSA-N |
Properties
| Boiling Point | 227.1±33.0°C (Predicted) |
| Density | 1.153±0.06 g/cm3 (Predicted) |
Reference Reading
1. Mild Copper-Catalyzed, l-Proline-Promoted Cross-Coupling of Methyl 3-Amino-1-benzothiophene-2-carboxylate
Vilija Kederienė, Indrė Jaglinskaitė, Paulina Voznikaitė, Jolanta Rousseau, Patrick Rollin, Algirdas Šačkus, Arnaud Tatibouët Molecules. 2021 Nov 11;26(22):6822. doi: 10.3390/molecules26226822.
Cu-catalyzed N-arylation is a useful tool for the chemical modification of aromatic heterocycles. Herein, an efficient carbon-nitrogen cross-coupling of methyl 3-amino-1-benzothiophene-2-carboxylate with a range of (hetero)aryl iodides using CuI, l-proline and Cs2CO3 in dioxane at moderate temperature is described. The procedure is an extremely general, relatively cheap, and experimentally simple way to afford the N-substituted products in moderate to high yields. The structures of the new heterocyclic compounds were confirmed by NMR spectroscopy and HRMS investigation.
2. A chemical probe targeting the PWWP domain alters NSD2 nucleolar localization
David Dilworth, Ronan P Hanley, Renato Ferreira de Freitas, et al. Nat Chem Biol. 2022 Jan;18(1):56-63. doi: 10.1038/s41589-021-00898-0. Epub 2021 Nov 15.
Nuclear receptor-binding SET domain-containing 2 (NSD2) is the primary enzyme responsible for the dimethylation of lysine 36 of histone 3 (H3K36), a mark associated with active gene transcription and intergenic DNA methylation. In addition to a methyltransferase domain, NSD2 harbors two proline-tryptophan-tryptophan-proline (PWWP) domains and five plant homeodomains (PHDs) believed to serve as chromatin reading modules. Here, we report a chemical probe targeting the N-terminal PWWP (PWWP1) domain of NSD2. UNC6934 occupies the canonical H3K36me2-binding pocket of PWWP1, antagonizes PWWP1 interaction with nucleosomal H3K36me2 and selectively engages endogenous NSD2 in cells. UNC6934 induces accumulation of endogenous NSD2 in the nucleolus, phenocopying the localization defects of NSD2 protein isoforms lacking PWWP1 that result from translocations prevalent in multiple myeloma (MM). Mutations of other NSD2 chromatin reader domains also increase NSD2 nucleolar localization and enhance the effect of UNC6934. This chemical probe and the accompanying negative control UNC7145 will be useful tools in defining NSD2 biology.
3. N-Methyl-(2S, 4R)-trans-4-hydroxy-L-proline, the major bioactive compound from Sideroxylon obtusifolium, attenuates pilocarpine-induced injury in cultured astrocytes
P E A Aquino, E A de Siqueira, L C F Paes, E P Magalhães, T M Barbosa, M A J de Carvalho, F V C Serra Azul, I Rosal Lustosa, M Mottin, T L Sampaio, A M C Martins, E R Silveira, G S B Viana Braz J Med Biol Res. 2022 Nov 4;55:e12381. doi: 10.1590/1414-431X2022e12381. eCollection 2022.
Glial cells have been implicated in temporal lobe epilepsy in humans and in its models. Astrocytes are lost in several brain regions after acute seizures induced by pilocarpine and may suffer hyperplasia at subsequent time points. This study investigated the effect of N-methyl-(2S,4R)-trans-4-hydroxy-L-proline (NMP) on astrocytes exposed to cytotoxic concentrations of pilocarpine. Astrocytes were incubated with pilocarpine (half maximal inhibitory concentration (IC50)=31.86 mM) for 24 h. Afterwards, they were treated with NMP at concentrations ranging from 3.12 to 100 μg/mL for 24 h. Cell viability was assessed by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Cytoplasmic reactive oxygen species (ROS) and mitochondrial transmembrane potential (ΔΨm) were analyzed by flow cytometry using 2',7'-dichlorofluorescein diacetate (DCFH-DA) and rhodamine-123 (Rho123), respectively. Expression of glial fibrillary acidic protein (GFAP) and voltage-dependent anion channel-1 (VDAC-1) were measured by western blot. Pilocarpine significantly decreased cell viability and mitochondrial potential and increased ROS concentration significantly by 6.7 times compared to the control. NMP concentrations ≥25 µg/mL protected astrocytes against pilocarpine-induced injury in a concentration-dependent manner. Concomitantly, NMP reduced cytoplasmic ROS accumulation to 27.3, 24.8, and 12.3% in the groups treated with 25, 50, and 100 µg/mL NMP, respectively. NMP also protected mitochondria from pilocarpine-induced depolarization. These effects were associated with improvement of pilocarpine-induced GFAP and VDAC-1 overexpression, which are important biomarkers of astrocyte dysfunction. In conclusion, the improvement of ROS accumulation, VDAC-1 overexpression, and mitochondrial depolarization are possible mechanisms of the NMP protective action on reactive astrocytes.
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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
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
