Fagomine

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 326758

CAS#: 53185-12-9

Description: Fagomine, also known as D-Fagomine, is an inhibitor of various Glycosidases, including rat intestinal surcase and bovine α-Fucosidase with IC50 of 90μM and 140 μM, respectively. D-Fagomine attenuates metabolic alterations induced by a high-energy-dense diet in rats. D-fagomine is present in common buckwheat-based foodstuffs in amounts ranging from 1 to 25 mg/kg or mg/L, it is stable during boiling, baking, frying and fermentation, and it is biosynthesised upon sprouting.


Price and Availability

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Fagomine is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 326758
Name: Fagomine
CAS#: 53185-12-9
Chemical Formula: C6H13NO3
Exact Mass: 147.0895
Molecular Weight: 147.174
Elemental Analysis: C, 48.97; H, 8.90; N, 9.52; O, 32.61


Synonym: Fagomine; 1,2,5-Trideoxy-1,5-imino-D-arabino-hexitol; D-Fagomine.

IUPAC/Chemical Name: (2R,3R,4R)-2-(hydroxymethyl)piperidine-3,4-diol

InChi Key: YZNNBIPIQWYLDM-HSUXUTPPSA-N

InChi Code: InChI=1S/C6H13NO3/c8-3-4-6(10)5(9)1-2-7-4/h4-10H,1-3H2/t4-,5-,6-/m1/s1

SMILES Code: O[C@H]1[C@H](O)[C@@H](CO)NCC1


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Mena-Barragán T, García-Moreno MI, Nanba E, Higaki K, Concia AL, Clapés P, García Fernández JM, Ortiz Mellet C. Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp(2)-iminosugar conjugates against glycosidases: A structure-activity relationship study in Gaucher fibroblasts. Eur J Med Chem. 2015 Aug 31. pii: S0223-5234(15)30222-1. doi: 10.1016/j.ejmech.2015.08.038. [Epub ahead of print] PubMed PMID: 26361824.

2: 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. D-Fagomine attenuates metabolic alterations induced by a high-energy-dense diet in rats. Food Funct. 2015 Aug;6(8):2614-9. doi: 10.1039/c5fo00591d. Epub 2015 Jul 1. PubMed PMID: 26130374.

3: Csatayová K, Davies SG, Fletcher AM, Ford JG, Klauber DJ, Roberts PM, Thomson JE. Asymmetric syntheses of (-)-3-epi-Fagomine, (2R,3S,4R)-dihydroxypipecolic acid, and several polyhydroxylated homopipecolic acids. J Org Chem. 2014 Nov 21;79(22):10932-44. doi: 10.1021/jo501952t. Epub 2014 Oct 30. PubMed PMID: 25337869.

4: Jiang FX, Liu QZ, Zhao D, Luo CT, Guo CP, Ye WC, Luo C, Chen H. A concise synthesis of N-substituted fagomine derivatives and the systematic exploration of their α-glycosidase inhibition. Eur J Med Chem. 2014 Apr 22;77:211-22. doi: 10.1016/j.ejmech.2014.03.004. Epub 2014 Mar 3. PubMed PMID: 24642564.

5: Ramos-Romero S, Molinar-Toribio E, Gómez L, Pérez-Jiménez J, Casado M, Clapés P, Piña B, Torres JL. 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. doi: 10.1002/oby.20640. Epub 2013 Dec 4. PubMed PMID: 24124117.

6: Kumar KS, Rathee JS, Subramanian M, Chattopadhyay S. Divergent synthesis of 4-epi-fagomine, 3,4-dihydroxypipecolic acid, and a dihydroxyindolizidine and their β-galactosidase inhibitory and immunomodulatory activities. J Org Chem. 2013 Aug 2;78(15):7406-13. doi: 10.1021/jo400448p. Epub 2013 Jul 15. PubMed PMID: 23806010.

7: Amézqueta S, Galán E, Vila-Fernández I, Pumarola S, Carrascal M, Abian J, Ribas-Barba L, Serra-Majem L, Torres JL. The presence of D-fagomine in the human diet from buckwheat-based foodstuffs. Food Chem. 2013 Feb 15;136(3-4):1316-21. doi: 10.1016/j.foodchem.2012.09.038. Epub 2012 Sep 18. PubMed PMID: 23194529.

8: Díez JA, Gálvez JA, Díaz-de-Villegas MD, Badorrey R, Bartholomew B, Nash RJ. 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. Org Biomol Chem. 2012 Dec 14;10(46):9278-86. doi: 10.1039/c2ob26732b. Epub 2012 Oct 29. PubMed PMID: 23104470.

9: Amézqueta S, Galán E, Fuguet E, Carrascal M, Abián J, Torres JL. Determination of D-fagomine in buckwheat and mulberry by cation exchange HPLC/ESI-Q-MS. Anal Bioanal Chem. 2012 Feb;402(5):1953-60. doi: 10.1007/s00216-011-5639-2. Epub 2011 Dec 30. PubMed PMID: 22207282.

10: Gómez L, Molinar-Toribio E, Calvo-Torras MÁ, Adelantado C, Juan ME, Planas JM, Cañas X, Lozano C, Pumarola S, Clapés P, Torres JL. D-Fagomine lowers postprandial blood glucose and modulates bacterial adhesion. Br J Nutr. 2012 Jun;107(12):1739-46. doi: 10.1017/S0007114511005009. Epub 2011 Oct 3. PubMed PMID: 22017795.

11: Castillo JA, Calveras J, Casas J, Mitjans M, Vinardell MP, Parella T, Inoue T, Sprenger GA, Joglar J, Clapés P. Fructose-6-phosphate aldolase in organic synthesis: preparation of D-fagomine, N-alkylated derivatives, and preliminary biological assays. Org Lett. 2006 Dec 21;8(26):6067-70. PubMed PMID: 17165931.

12: Goujon JY, Gueyrard D, Compain P, Martin OR, Ikeda K, Kato A, Asano N. General synthesis and biological evaluation of alpha-1-C-substituted derivatives of fagomine (2-deoxynojirimycin-alpha-C-glycosides). Bioorg Med Chem. 2005 Mar 15;13(6):2313-24. PubMed PMID: 15727880.

13: Takahata H, Banba Y, Ouchi H, Nemoto H, Kato A, Adachi I. Asymmetric synthesis of the four possible fagomine isomers. J Org Chem. 2003 May 2;68(9):3603-7. PubMed PMID: 12713367.

14: Taniguchi S, Asano N, Tomino F, Miwa I. Potentiation of glucose-induced insulin secretion by fagomine, a pseudo-sugar isolated from mulberry leaves. Horm Metab Res. 1998 Nov;30(11):679-83. PubMed PMID: 9918385.

15: Kato A, Asano N, Kizu H, Matsui K. Fagomine isomers and glycosides from Xanthocercis zambesiaca. J Nat Prod. 1997 Mar;60(3):312-4. PubMed PMID: 9157194.