CAS Number53185-12-9
Synonyms1,5-imino-1,2,5-trideoxy-D-arabino hexitol; (2r,3r,4r)-2-(hydroxymethyl)piperidine-3,4-diol; Fagomine; 1,2,5-Trideoxy-1,5-imino-D-arabino-hexitol; (2R,3R,4R)-2-(Hydroxymethyl)-3,4-piperidinediol
Molecular FormulaC6H13O3N1
Molecular Weight147.17
Density1.3±0.1 g/cm3
Boiling Point315.4±42.0 °C at 760 mmHg
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 53185-12-9 |
| Catalog No. | 2A-2198858 |
| Chinese Name | (2R,3R,4R)-2-羟甲基哌啶-3,4-二醇 |
| Synonyms | 1,5-imino-1,2,5-trideoxy-D-arabino hexitol; (2r,3r,4r)-2-(hydroxymethyl)piperidine-3,4-diol; Fagomine; 1,2,5-Trideoxy-1,5-imino-D-arabino-hexitol; (2R,3R,4R)-2-(Hydroxymethyl)-3,4-piperidinediol |
| Molecular Formula | C6H13O3N1 |
| Molecular Weight | 147.17 |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 315.4±42.0 °C at 760 mmHg |
| Storage Condition | -20°C |
| Application | Fagomine is a mild glycosidase (glycosidase) inhibitor. Fagomine acts on Amyloglucosidase (A.niger), β-Glucosidase (bovine) and Isomaltase (yeast), with Ki of 4.8 μM, 39 μM and 70 μM respectively. |
| HTC | 2933399090 |
| MDL Number | MFCD18782654 |
| SMILES | OCC1NCCC(O)C1O |
| InChI | InChI=1S/C6H13NO3/c8-3-4-6(10)5(9)1-2-7-4/h4-10H,1-3H2/t4-,5-,6-/m1/s1 |
| InChI Key | YZNNBIPIQWYLDM-HSUXUTPPSA-N |
| MSDS | msds/200802_1_53185_12_9.pdf |
| Use of | Fagomine is a mild glycosidase inhibitor. The Ki of the iminosugar Fagomine is 4.8 μM, 39 μM, and 70 μM for Amyloglucosidase (A.niger), β-Glucosidase (bovine), and Isomaltase (yeast), respectively. Properties Name (2R,3R,4R)-2-(hydroxymethyl)piperidine-3,4-diol Synonym More Synonyms Fagomine Biological Activity Description Fagomine is a mild glycosidase inhibitor. The Ki of the iminosugar Fagomine is 4.8 μM, 39 μM, and 70 μM for Amyloglucosidase (A.niger), β-Glucosidase (bovine), and Isomaltase (yeast), respectively. Related Catalog Signaling Pathways >> Others >> Others Research Areas >> Metabolic Disease Natural Products >> Saccharides and Glycosides Glycosidase[1] In Vitro Fagomine (D-fagomine) is an iminosugar that has been shown to selectively agglutinate Enterobacteriales in vitro. Fagomine selectively agglutinates fimbriated enterobacteria (e.g., E.coli) and inhibits their adhesion to the intestinal mucosa; the reason for this is probably related to its structural similarity with lectin-binding saccharides (e.g., mannose). Fagomine is capable of altering this effect of high-fat high-sucrose diet (HFHS) on the proportion of Enterobacteriales and E.coli[2]. In Vivo Fagomine (D-fagomine) is a natural iminosugar that counteracts the short-term effects of a high-energy-dense diet on body weight, fasting blood glucose levels and the proportion of gut Enterobacteriales[3]. Compare to the standard group, rats fed high-fat high-sucrose diet (HFHS) with Fagomine (D-fagomine) gain significantly less weight (15.3%) than those fed HFHS (20.9%)[2]. Cell Assay Human skin fibroblasts from a healthy and three Gaucher disease patients (with N188S/G183W, V230G/R296X and L444P/L444P mutations) are maintained in our laboratory with DMEM supplemented with 10% FBS as the culture medium. For enzyme activity enhancement assay, cells are cultured in the presence of different concentrations of Fagomine or DMSO alone (as a control) for 5 days and harvested by scraping. Cytotoxicity of Fagomine is monitored by measuring the lactate dehydrogenase activities in the cultured supernatants[1]. References [2]. Ramos-Romero S, et al. Effect of (D)-fagomine on excreted Enterobacteria and weight gain in rats fed a high-fat high-sucrose diet. Obesity (Silver Spring). 2014 Apr;22(4):976-9. [3]. Molinar-Toribio E, et al. D-Fagomine attenuates metabolic alterations induced by a high-energy-dense diet in rats. Food Funct. 2015 Aug;6(8):2614-9. Chemical & Physical Properties Molecular Formula C6H13NO3 Exact Mass 147.089539 PSA 72.72000 LogP -1.63 Index of Refraction 1.535 InChIKey YZNNBIPIQWYLDM-HSUXUTPPSA-N SMILES OCC1NCCC(O)C1O Safety Information HS Code 2933399090 Synthetic Route (3aR,4R,7aR)-me... 1333312-83-6 53185-12-9 Literature: Kundu, Pintu K.; Ghosh, Sunil K. Tetrahedron Asymmetry, 2011 , vol. 22, # 10 p. 1090 - 1096 (3S,4R)-6-[(ben... 121742-14-1 53185-12-9 Literature: Heterocycles, , vol. 28, # 1 p. 477 - 480 (2R,3R,4R)-benz... 1430587-89-5 53185-12-9 Literature: Min, Im Sook; Kim, Seung In; Hong, Seungmin; Kim, In Su; Jung, Young Hoon Tetrahedron, 2013 , vol. 69, # 19 p. 3901 - 3906 Precursor & DownStream Precursor 6 CAS#:121742-14-1 (3S,4R)-6-[(ben... CAS#:1129725-82-1 (2S,3R,4R)-1-be... CAS#:354153-40-5 (1R,2R,6S)-2-(t... CAS#:143706-32-5 2-Desoxy-L-thre... DownStream 0 |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Summary 2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
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