Fagomine

• CAT Number: I003947
• CAS Number: 53185-12-9
• Molecular Formula: C6H13NO3
• Molecular Weight: 147.17
• Purity: ≥95%
• Target: Glycosidase inhibitor
• Solubility: H2O: ≥ 36 mg/mL
• Storage: 3 years -20℃ powder
• IUPAC Name: (2R,3R,4R)-2-(hydroxymethyl)piperidine-3,4-diol
• InChI: InChI=1S/C6H13NO3/c8-3-4-6(10)5(9)1-2-7-4/h4-10H,1-3H2/t4-,5-,6-/m1/s1
• InChIKey: YZNNBIPIQWYLDM-HSUXUTPPSA-N
• SMILES: O[C@H]1[C@H](O)[C@@H](CO)NCC1

Fagomine (Cat.No:I003947) is a natural alkaloid found in certain plants and bacteria. It exhibits anti-inflammatory and antimicrobial properties. Fagomine has been studied for its potential in regulating blood sugar levels and has shown promising results in animal models. 

Reference

1:FATE OF D-FAGOMINE AFTER ORAL ADMINISTRATION TO RATS. Amézqueta S, Ramos-Romero S, Martínez-Guimet C, Moreno A, Hereu M, Torres JL.J Agric Food Chem. 2017 May 10. doi: 10.1021/acs.jafc.7b01026. [Epub ahead of print] PMID: 28489364 2:Synthesis and evaluation of N-alkylated analogues of aza-galacto-fagomine – potential pharmacological chaperones for Krabbe disease. Viuff AH, Jensen HH.Org Biomol Chem. 2016 Sep 28;14(36):8545-56. doi: 10.1039/c6ob01309k. Epub 2016 Aug 22. PMID: 27545315 3:Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp(2)-iminosugar conjugates against glycosidases: A structure-activity relationship study in Gaucher fibroblasts. Mena-Barragán T, García-Moreno MI, Nanba E, Higaki K, Concia AL, Clapés P, García Fernández JM, Ortiz Mellet C.Eur J Med Chem. 2016 Oct 4;121:880-91. doi: 10.1016/j.ejmech.2015.08.038. Epub 2015 Aug 31. PMID: 26361824 4:D-Fagomine attenuates metabolic alterations induced by a high-energy-dense diet in rats. Molinar-Toribio E, Pérez-Jiménez J, Ramos-Romero S, Gómez L, Taltavull N, Nogués MR, Adeva A, Jáuregui O, Joglar J, Clapés P, Torres JL.Food Funct. 2015 Aug;6(8):2614-9. doi: 10.1039/c5fo00591d. Epub 2015 Jul 1. PMID: 26130374 5:Asymmetric syntheses of (-)-3-epi-Fagomine, (2R,3S,4R)-dihydroxypipecolic acid, and several polyhydroxylated homopipecolic acids. Csatayová K, Davies SG, Fletcher AM, Ford JG, Klauber DJ, Roberts PM, Thomson JE.J Org Chem. 2014 Nov 21;79(22):10932-44. doi: 10.1021/jo501952t. Epub 2014 Oct 30. PMID: 25337869 6:A concise synthesis of N-substituted fagomine derivatives and the systematic exploration of their α-glycosidase inhibition. Jiang FX, Liu QZ, Zhao D, Luo CT, Guo CP, Ye WC, Luo C, Chen H.Eur J Med Chem. 2014 Apr 22;77:211-22. doi: 10.1016/j.ejmech.2014.03.004. Epub 2014 Mar 3. PMID: 24642564 7:Effect of (D)-fagomine on excreted Enterobacteria and weight gain in rats fed a high-fat high-sucrose diet. Ramos-Romero S, Molinar-Toribio E, Gómez L, Pérez-Jiménez J, Casado M, Clapés P, Piña B, Torres JL.Obesity (Silver Spring). 2014 Apr;22(4):976-9. doi: 10.1002/oby.20640. Epub 2013 Dec 4. PMID: 24124117 Free Article8:Divergent synthesis of 4-epi-fagomine, 3,4-dihydroxypipecolic acid, and a dihydroxyindolizidine and their β-galactosidase inhibitory and immunomodulatory activities. Kumar KS, Rathee JS, Subramanian M, Chattopadhyay S.J Org Chem. 2013 Aug 2;78(15):7406-13. doi: 10.1021/jo400448p. Epub 2013 Jul 15. PMID: 23806010 9:The presence of D-fagomine in the human diet from buckwheat-based foodstuffs. Amézqueta S, Galán E, Vila-Fernández I, Pumarola S, Carrascal M, Abian J, Ribas-Barba L, Serra-Majem L, Torres JL.Food Chem. 2013 Feb 15;136(3-4):1316-21. doi: 10.1016/j.foodchem.2012.09.038. Epub 2012 Sep 18. PMID: 23194529 10:Stereoselective synthesis and biological evaluation of D-fagomine, D-3-epi-fagomine and D-3,4-epi-fagomine analogs from D-glyceraldehyde acetonide as a common building block. Díez JA, Gálvez JA, Díaz-de-Villegas MD, Badorrey R, Bartholomew B, Nash RJ.Org Biomol Chem. 2012 Dec 14;10(46):9278-86. doi: 10.1039/c2ob26732b. Epub 2012 Oct 29. PMID: 23104470