Pentosidine

Source: Wikipedia, the free encyclopedia.
Pentosidine
Names
Systematic IUPAC name
(2S)-2-Amino-6-(2-{[(4S)-4-amino-4-carboxybutyl]amino}-4H-imidazo[4,5-b]pyridin-4-yl)hexanoic acid
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
UNII
  • InChI=1S/C17H26N6O4/c18-11(15(24)25)5-1-2-9-23-10-4-7-13-14(23)22-17(21-13)20-8-3-6-12(19)16(26)27/h4,7,10-12H,1-3,5-6,8-9,18-19H2,(H,20,21)(H,24,25)(H,26,27)/t11-,12-/m0/s1 ☒N
    Key: AYEKKSTZQYEZPU-RYUDHWBXSA-N ☒N
  • InChI=1/C17H26N6O4/c18-11(15(24)25)5-1-2-9-23-10-4-7-13-14(23)22-17(21-13)20-8-3-6-12(19)16(26)27/h4,7,10-12H,1-3,5-6,8-9,18-19H2,(H,20,21)(H,24,25)(H,26,27)/t11-,12-/m0/s1
    Key: AYEKKSTZQYEZPU-RYUDHWBXBF
  • C1=CN(C2=NC(=NC2=C1)NCCC[C@@H](C(=O)O)N)CCCC[C@@H](C(=O)O)N
Properties
C17H26N6O4
Molar mass 378.433 g·mol−1
Density 1.47 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pentosidine is a

advanced glycation endproducts
, or AGEs. It is a well characterized and easily detected member of this large class of compounds.

Background

AGEs are biochemicals formed continuously under normal circumstances, but more rapidly under a variety of stresses, especially oxidative stress and hyperglycemia. They serve as markers of stress and act as toxins themselves. Pentosidine is typical of the class, except that it fluoresces, which allows it to be seen and measured easily. Because it is well characterized, it is often studied to provide new insight into the biochemistry of AGE compounds in general.

Biochemistry

Derived from ribose, a pentose, pentosidine forms fluorescent cross-links between the arginine and lysine residues in collagen. It is formed in a reaction of the amino acids with the Maillard reaction products of ribose.[1]

Although it is present only in trace concentrations among tissue proteins, it is useful for assessing cumulative damage to proteins—

non-enzymatic browning reactions with carbohydrates.[2][3][4]

Physiology

In vivo, AGEs form pentosidine through sugar fragmentation. In patients with

diabetes mellitus type 2, pentosidine correlates with the presence and severity of diabetic complications.[5]

References

  1. PMID 9461101
    .
  2. PMID 1904867
    . Retrieved 2007-12-14.
  3. ^ Will Boggs. "DHEA Restores Oxidative Balance in Type 2 Diabetes". Medscape. Retrieved 2007-12-14.[dead link]
  4. PMID 15243705
    .
  5. PMID 1397702. Archived from the original
    on 2008-08-07. Retrieved 2007-12-15.
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