Fructoselysine

Fructoselysine
Names
	IUPAC name N6-(1-Deoxy-D-fructos-1-yl)-L-lysine
	Systematic IUPAC name (2S)-2-Amino-6-{[(3S,4R,5R)-3,4,5,6-tetrahydroxy-2-oxohexyl]amino}hexanoic acid
	Other names Fructosyllysine; ε-Fructosyl-L-lysine
Identifiers
CAS Number	21291-40-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	8015298;
PubChem CID	9839580;
UNII	F2RDS6J0Y0 ;
	InChI 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 Key: BFSYFTQDGRDJNV-AYHFEMFVSA-N;
	SMILES C(CCNCC(=O)[C@H]([C@@H]([C@@H](CO)O)O)O)C[C@@H](C(=O)O)N;
Properties
Chemical formula	C12H24N2O7
Molar mass	308.331 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Fructoselysine is an Amadori adduct of glucose to lysine.^[1]

It breaks down into furosine on acid-catalysed hydrolysis.^[2] 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.^[3]

References

↑ Wiame, E; Delpierre, G; Collard, F; Van Schaftingen, E (8 November 2002). "Identification of a pathway for the utilization of the Amadori product fructoselysine in Escherichia coli". The Journal of Biological Chemistry. 277 (45): 42523–9. doi:10.1074/jbc.m200863200. PMID 12147680.
↑ Oimomi, M.; Hatanaka, H.; Ishikawa, K.; Kubota, S.; Yoshimura, Y.; Baba, S. (May 1984). "Increased fructose-lysine of nail protein in diabetic patients". Klinische Wochenschrift. 62 (10): 477–478. doi:10.1007/BF01726910. PMID 6431176. S2CID 36668875.
↑ Wiame, E; Van Schaftingen, E (15 March 2004). "Fructoselysine 3-epimerase, an enzyme involved in the metabolism of the unusual Amadori compound psicoselysine in Escherichia coli". The Biochemical Journal. 378 (Pt 3): 1047–52. doi:10.1042/bj20031527. PMC 1224009. PMID 14641112.

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[Identification_of_a_pathway_for_the_utilization_of_the_Amadori_product_fructoselysine_in_Escherichia_coli.-1] Wiame, E; Delpierre, G; Collard, F; Van Schaftingen, E (8 November 2002). "Identification of a pathway for the utilization of the Amadori product fructoselysine in Escherichia coli". The Journal of Biological Chemistry. 277 (45): 42523–9. doi:10.1074/jbc.m200863200. PMID 12147680.

[Increased_fructose-lysine_of_nail_protein_in_diabetic_patients-2] Oimomi, M.; Hatanaka, H.; Ishikawa, K.; Kubota, S.; Yoshimura, Y.; Baba, S. (May 1984). "Increased fructose-lysine of nail protein in diabetic patients". Klinische Wochenschrift. 62 (10): 477–478. doi:10.1007/BF01726910. PMID 6431176. S2CID 36668875.

[Fructoselysine_3-epimerase,_an_enzyme_involved_in_the_metabolism_of_the_unusual_Amadori_compound_psicoselysine_in_Escherichia_coli.-3] Wiame, E; Van Schaftingen, E (15 March 2004). "Fructoselysine 3-epimerase, an enzyme involved in the metabolism of the unusual Amadori compound psicoselysine in Escherichia coli". The Biochemical Journal. 378 (Pt 3): 1047–52. doi:10.1042/bj20031527. PMC 1224009. PMID 14641112.

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References