3-Deoxyglucosone

Source: Wikipedia, the free encyclopedia.
3-Deoxyglucosone
Names
IUPAC name
3-Deoxy-D-erythro-hexos-2-ulose
Systematic IUPAC name
(4S,5R)-4,5,6-Trihydroxy-2-oxohexanal
Other names
3-Deoxy-D-erythro-hexosulose; 2-Keto-3-deoxyglucose; 3-Deoxy-D-erythro-hexosulose; 3-Deoxy-D-glucosone; D-3-Deoxyglucosone
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
ECHA InfoCard
 100.241.539 Edit this at Wikidata
UNII
  • InChI=1S/C6H10O5/c7-2-4(9)1-5(10)6(11)3-8/h2,5-6,8,10-11H,1,3H2/t5-,6+/m0/s1 checkY
    Key: ZGCHLOWZNKRZSN-NTSWFWBYSA-N checkY
  • InChI=1/C6H10O5/c7-2-4(9)1-5(10)6(11)3-8/h2,5-6,8,10-11H,1,3H2/t5-,6+/m0/s1
    Key: ZGCHLOWZNKRZSN-NTSWFWBYBM
  • C(C(C(CO)O)O)C(=O)C=O
  • O=C(C=O)C[C@H](O)[C@H](O)CO
Properties
C6H10O5
Molar mass 162.141 g·mol−1
Density 1.406 g/ml
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

3-Deoxyglucosone (3DG) is a sugar that is notable because it is a marker for diabetes. 3DG reacts with protein to form

aging.[1]

Biosynthesis

4-Imidazolone arise from the condensation of arginine residues and 3-deoxyglucosone (R = CH2CH(OH)CH(OH)CH2OH).[2]

3DG is made naturally via the Maillard reaction. It forms after glucose reacts with primary amino groups of lysine or arginine found in proteins. Because of the increased concentration of the reactant glucose, more 3DG forms with excessive blood sugar levels, as in uncontrolled diabetes. Glucose reacts non-enzymatically with protein amino groups to initiate glycation. The formation of 3DG may account for the numerous complications of diabetes as well as aging.[1]

3DG arises also via the degradation of fructose 3-phosphate (F3P).[3] 3DG plays a central role in the development of diabetic complications via the action of fructosamine-3-kinase.[citation needed]

Biochemistry

As a dicarbonyl sugar, i.e. one with the grouping R-C(O)-C(O)-R, 3DG is highly reactive toward amine groups. Amines are common in amino acids as well as some nucleic acids. The products from the reaction of 3DG with protein amino groups are called

aging.[1]

3DG has a variety of potential biological effects, particularly when it is present at elevated concentrations in diabetic states:

3DG and ROS

3DG induces

atherosclerotic plaques. This observation suggests that an increase in 3DG may trigger atherogenesis in diabetes.[15][16] 3DG also inactivates some enzymes that protect cells from ROS. For example, glutathione peroxidase, a central antioxidant enzyme that uses glutathione to remove ROS, and glutathione reductase, which regenerates glutathione, are both inactivated by 3DG.[17][18] Diabetic humans show increased oxidative stress.[19] 3DG-induced ROS result in oxidative DNA damage.[20] 3DG can be internalized by cells and internalized 3DG is responsible for the production of intracellular oxidative stress.[21]

Detoxification

Although of uncertain medical significance, a variety of compounds react with 3DG, possibly deactivating it. One such agent is

aminoguanidine (AG).[22] AG reduces AGE associated retinal, neural, arterial, and renal pathologies in animal models.[23][24][25][26] The problem with AG is that it is toxic in the quantities needed for efficacy.[citation needed
]

Additional reading

References

  1. ^
    PMID 10491986
    .
  2. S2CID 58631777
    .
  3. PMID 2300805
    .
  4. PMID 12766129
    .
  5. PMID 8070616
    .
  6. PMID 11911173
    .
  7. PMID 16249455
    .
  8. PMID 7827091
    .
  9. PMID 9186486
    .
  10. PMID 9836531
    .
  11. PMID 8769121
    .
  12. S2CID 39613521
    .
  13. PMID 9538214
    .
  14. PMID 9430981
    .
  15. S2CID 21268446
    .
  16. PMID 9218489
    .
  17. PMID 9175718
    .
  18. PMID 11168980
    .
  19. PMID 12204421
    .
  20. PMID 11506829
    .
  21. PMID 16452312
    .
  22. S2CID 84490567
    .
  23. PMID 1943726
    .
  24. PMID 1834497
    .
  25. PMID 1541387
    .
  26. PMID 3487117
    .
Retrieved from "https://en.wikipedia.org/w/index.php?title=3-Deoxyglucosone&oldid=1203578488"