Glucosepane

Glucosepane
Names
	IUPAC name (2S)-2-Amino-6-((6R,7S)-2-(((S)-4-amino-4-carboxybutyl)amino)-6,7-dihydroxy-6,7,8,8a-tetrahydroimidazo[4,5-b]azepin-4(5H)-yl)hexanoic acid
	Other names Glucosepan
Identifiers
CAS Number	257290-23-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	26333276 ;
PubChem CID	135565852;
UNII	66K23JT22H ;
CompTox Dashboard (EPA)	DTXSID80894863 ;
	InChI InChI=1S/C18H32N6O6/c19-10(16(27)28)4-1-2-7-24-9-14(26)13(25)8-12-15(24)23-18(22-12)21-6-3-5-11(20)17(29)30/h10-14,25-26H,1-9,19-20H2,(H,21,22)(H,27,28)(H,29,30)/t10-,11-,12?,13-,14+/m0/s1 Key: JTMICRULXGWYCN-WSOGJNRSSA-N ; InChI=1/C18H32N6O6/c19-10(16(27)28)4-1-2-7-24-9-14(26)13(25)8-12-15(24)23-18(22-12)21-6-3-5-11(20)17(29)30/h10-14,25-26H,1-9,19-20H2,(H,21,22)(H,27,28)(H,29,30)/t10-,11-,12?,13-,14+/m0/s1 Key: JTMICRULXGWYCN-WSOGJNRSBX;
	SMILES C1[C@@H]([C@@H](CN(C2=NC(=NC21)NCCC[C@@H](C(=O)O)N)CCCC[C@@H](C(=O)O)N)O)O;
Properties
Chemical formula	C18H32N6O6
Molar mass	428.490 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Glucosepane is a lysine-arginine protein cross-linking product and advanced glycation end product (AGE) derived from D-glucose.^[1] It is an irreversible, covalent cross-link product that has been found to make intermolecular and intramolecular cross-links in the collagen of the extracellular matrix (ECM) and crystallin of the eyes.^[2] Covalent protein cross-links irreversibly link proteins together in the ECM of tissues. Glucosepane is present in human tissues at levels 10 to 1000 times higher than any other cross-linking AGE, and is currently considered to be the most important cross-linking AGE.^[3]

^ Lederer, M.O., Bühler, H.P. (1999). "Cross-linking of proteins by maillard processes - Characterization and detection of a lysine-arginine cross-link derived from D-glucose". Bioorganic and Medicinal Chemistry. 7 (6): 1081–1088. doi:10.1016/S0968-0896(99)00040-1. PMID 10428377.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Sell, D. R., Biemel, K. M., Reihl, O., Lederer, M. O., Strauch, C. M., & Monnier, V. M. (2005). "Glucosepane is a major protein cross-link of the senescent human extracellular matrix: Relationship with diabetes". Journal of Biological Chemistry. 280 (13): 12310–12315. doi:10.1074/jbc.M500733200. PMID 15677467.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Monnier, V. M., Mustata, G. T., Biemel, K. L., Reihl, O., Lederer, M. O., Zhenyu, D.; et al. (2005). "Cross-linking of the extracellular matrix by the maillard reaction in aging and diabetes: An update on "a puzzle nearing resolution"". Annals of the New York Academy of Sciences. 1043: 533–544. Bibcode:2005NYASA1043..533M. doi:10.1196/annals.1333.061. PMID 16037276. S2CID 27507321.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[1] Lederer, M.O., Bühler, H.P. (1999). "Cross-linking of proteins by maillard processes - Characterization and detection of a lysine-arginine cross-link derived from D-glucose". Bioorganic and Medicinal Chemistry. 7 (6): 1081–1088. doi:10.1016/S0968-0896(99)00040-1. PMID 10428377.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[2] Sell, D. R., Biemel, K. M., Reihl, O., Lederer, M. O., Strauch, C. M., & Monnier, V. M. (2005). "Glucosepane is a major protein cross-link of the senescent human extracellular matrix: Relationship with diabetes". Journal of Biological Chemistry. 280 (13): 12310–12315. doi:10.1074/jbc.M500733200. PMID 15677467.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[3] Monnier, V. M., Mustata, G. T., Biemel, K. L., Reihl, O., Lederer, M. O., Zhenyu, D.; et al. (2005). "Cross-linking of the extracellular matrix by the maillard reaction in aging and diabetes: An update on "a puzzle nearing resolution"". Annals of the New York Academy of Sciences. 1043: 533–544. Bibcode:2005NYASA1043..533M. doi:10.1196/annals.1333.061. PMID 16037276. S2CID 27507321.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[1]

[2]

[3]