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  Y
3D model (JSmol)	Interactive image
ChemSpider	8015298
PubChem CID	9839580
UNII	F2RDS6J0Y0  Y
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

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.
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.
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.