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MedKoo Cat#: 597572 | Name: Fructosyl-lysine

Description:

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

Fructosyl-lysine is an Amadori adduct of glucose to lysine. It breaks down into furosine on acid-catalysed hydrolysis. E. coli breaks it down using the enzymes fructoselysine-6-kinase and fructoselysine 6-phosphate deglycase into glucose 6-phosphate and lysine, a set of enzymes located on the frl (fructoselysine) operon.

Chemical Structure

Fructosyl-lysine
Fructosyl-lysine
CAS#21291-40-7 (free)

Theoretical Analysis

MedKoo Cat#: 597572

Name: Fructosyl-lysine

CAS#: 21291-40-7 (free)

Chemical Formula: C12H24N2O7

Exact Mass: 308.1584

Molecular Weight: 308.33

Elemental Analysis: C, 46.75; H, 7.85; N, 9.09; O, 36.32

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
23931-62-6 (acetate) 21291-40-7 (free) 96192-35-7 (2HCl)
Synonym
Fructosyl-lysine; Fructose lysine; Fructosyllysine; Nε-(1-Deoxy-D-fructos-1-yl)-L-lysine; ε-Fructoselysine; ε-N-Deoxyfructosyllysine;
IUPAC/Chemical Name
N6-((3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexyl)-L-lysine
InChi Key
BFSYFTQDGRDJNV-AYHFEMFVSA-N
InChi Code
InChI=1S/C12H24N2O7/c13-7(12(20)21)3-1-2-4-14-5-8(16)10(18)11(19)9(17)6-15/h7,9-11,14-15,17-19H,1-6,13H2,(H,20,21)/t7-,9+,10+,11+/m0/s1
SMILES Code
N[C@@H](CCCCNCC([C@H]([C@@H]([C@@H](CO)O)O)O)=O)C(O)=O
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 308.33 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
1: Rabbani N, Thornalley PJ. Hidden complexities in the measurement of fructosyl-lysine and advanced glycation end products for risk prediction of vascular complications of diabetes. Diabetes. 2015 Jan;64(1):9-11. doi: 10.2337/db14-1516. PubMed PMID: 25538281. 2: Watanabe B, Ichiyanagi A, Hirokawa K, Gomi K, Nakatsu T, Kato H, Kajiyama N. Synthesis and inhibitory activity of substrate-analog fructosyl peptide oxidase inhibitors. Bioorg Med Chem Lett. 2015 Sep 15;25(18):3910-3. doi: 10.1016/j.bmcl.2015.07.045. Epub 2015 Jul 23. PubMed PMID: 26235953. 3: Sakai Y, Yoshida N, Tani Y, Kato N. Production of fructosyl lysine oxidase from Fusarium oxysporum S-1F4 on autoclave-browned medium. Biosci Biotechnol Biochem. 1996 Jan;60(1):150-1. PubMed PMID: 8824836. 4: Bui TP, Ritari J, Boeren S, de Waard P, Plugge CM, de Vos WM. Production of butyrate from lysine and the Amadori product fructoselysine by a human gut commensal. Nat Commun. 2015 Dec 1;6:10062. doi: 10.1038/ncomms10062. PubMed PMID: 26620920; PubMed Central PMCID: PMC4697335. 5: Karachalias N, Babaei-Jadidi R, Ahmed N, Thornalley PJ. Accumulation of fructosyl-lysine and advanced glycation end products in the kidney, retina and peripheral nerve of streptozotocin-induced diabetic rats. Biochem Soc Trans. 2003 Dec;31(Pt 6):1423-5. Review. PubMed PMID: 14641079. 6: Sakai Y, Yoshida N, Isogai A, Tani Y, Kato N. Purification and properties of fructosyl lysine oxidase from Fusarium oxysporum S-1F4. Biosci Biotechnol Biochem. 1995 Mar;59(3):487-91. PubMed PMID: 7766189. 7: Miura S, Ferri S, Tsugawa W, Kim S, Sode K. Development of fructosyl amine oxidase specific to fructosyl valine by site-directed mutagenesis. Protein Eng Des Sel. 2008 Apr;21(4):233-9. doi: 10.1093/protein/gzm047. Epub 2008 Jan 31. PubMed PMID: 18239075. 8: Yoshida N, Takatsuka K, Katsuragi T, Tani Y. Occurrence of fructosyl-amino acid oxidase-reactive compounds in fungal cells. Biosci Biotechnol Biochem. 2005 Jan;69(1):258-60. PubMed PMID: 15665502. 9: Ogawa K, Stöllner D, Scheller F, Warsinke A, Ishimura F, Tsugawa W, Ferri S, Sode K. Development of a flow-injection analysis (FIA) enzyme sensor for fructosyl amine monitoring. Anal Bioanal Chem. 2002 Jul;373(4-5):211-4. Epub 2002 Jun 6. PubMed PMID: 12110969. 10: Fujiwara M, Sumitani J, Koga S, Yoshioka I, Kouzuma T, Imamura S, Kawaguchi T, Arai M. Alteration of substrate specificity of fructosyl-amino acid oxidase from Fusarium oxysporum. Appl Microbiol Biotechnol. 2007 Mar;74(4):813-9. Epub 2006 Dec 9. PubMed PMID: 17160532. 11: Hirokawa K, Gomi K, Bakke M, Kajiyama N. Distribution and properties of novel deglycating enzymes for fructosyl peptide in fungi. Arch Microbiol. 2003 Sep;180(3):227-31. Epub 2003 Jul 17. PubMed PMID: 12879216. 12: Takei I, Hoshino T, Tominaga M, Ishibashi M, Kuwa K, Umemoto M, Tani W, Okahashi M, Yasukawa K, Kohzuma T, Sato A. Committee on Diabetes Mellitus Indices of the Japan Society of Clinical Chemistry-recommended reference measurement procedure and reference materials for glycated albumin determination. Ann Clin Biochem. 2016 Jan;53(Pt 1):124-32. doi: 10.1177/0004563215599178. Epub 2015 Jul 17. PubMed PMID: 26187553. 13: Vhangani LN, Van Wyk J. Antioxidant activity of Maillard reaction products (MRPs) derived from fructose-lysine and ribose-lysine model systems. Food Chem. 2013 Apr 15;137(1-4):92-8. doi: 10.1016/j.foodchem.2012.09.030. Epub 2012 Sep 16. PubMed PMID: 23199995. 14: Erbersdobler HF, Hupe A. Determination of lysine damage and calculation of lysine bio-availability in several processed foods. Z Ernahrungswiss. 1991 Feb;30(1):46-9. PubMed PMID: 1907058. 15: Kojima K, Mikami-Sakaguchi A, Kameya M, Miyamoto Y, Ferri S, Tsugawa W, Sode K. Substrate specificity engineering of Escherichia coli derived fructosamine 6-kinase. Biotechnol Lett. 2013 Feb;35(2):253-8. doi: 10.1007/s10529-012-1062-9. Epub 2012 Oct 18. PubMed PMID: 23076362. 16: Jeong HY, Song MH, Back JH, Han DM, Wu X, Monnier V, Jahng KY, Chae KS. The veA gene is necessary for the inducible expression by fructosyl amines of the Aspergillus nidulans faoA gene encoding fructosyl amino acid oxidase (amadoriase, EC 1.5.3). Arch Microbiol. 2002 Nov;178(5):344-50. Epub 2002 Aug 10. PubMed PMID: 12375102. 17: Oimomi M, Nishimoto S, Kitamura Y, Matsumoto S, Hatanaka H, Baba S. Increased fructose-lysine of nail protein and blood glucose control in diabetic patients. Horm Metab Res. 1986 Dec;18(12):827-9. PubMed PMID: 3102337. 18: Sakaguchi-Mikami A, Kameya M, Ferri S, Tsugawa W, Sode K. Cloning and characterization of fructosamine-6-kinase from Arthrobacter aurescens. Appl Biochem Biotechnol. 2013 Jun;170(3):710-7. doi: 10.1007/s12010-013-0229-8. Epub 2013 Apr 23. PubMed PMID: 23609907. 19: Hellwig M, Bunzel D, Huch M, Franz CM, Kulling SE, Henle T. Stability of Individual Maillard Reaction Products in the Presence of the Human Colonic Microbiota. J Agric Food Chem. 2015 Aug 5;63(30):6723-30. doi: 10.1021/acs.jafc.5b01391. Epub 2015 Jul 24. PubMed PMID: 26186075. 20: Miller KA, Phillips RS, Kilgore PB, Smith GL, Hoover TR. A Mannose Family Phosphotransferase System Permease and Associated Enzymes Are Required for Utilization of Fructoselysine and Glucoselysine in Salmonella enterica Serovar Typhimurium. J Bacteriol. 2015 Sep;197(17):2831-9. doi: 10.1128/JB.00339-15. Epub 2015 Jun 22. PubMed PMID: 26100043; PubMed Central PMCID: PMC4524042.

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