Fagomine free base

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MedKoo CAT#: 326758

CAS#: 53185-12-9 (free base)

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.

Chemical Structure

Fagomine free base
CAS# 53185-12-9 (free base)

Theoretical Analysis

MedKoo Cat#: 326758
Name: Fagomine free base
CAS#: 53185-12-9 (free base)
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

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
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Related CAS #: 53185-12-9 (free base)   53185-13-0 (HCl)   1337470-51-5 (tartrate)    

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 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

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).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 147.174 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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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.