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Erythrose

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Erythrose

Erythrose[1]

D-Erythrose

L-Erythrose
Names
IUPAC names
(2R,3R)-2,3,4-Trihydroxybutanal (D)
(2S,3S)-2,3,4-Trihydroxybutanal (L)
Identifiers
(D) Y
(L) Y
ChEBI  Y
ChemSpider (D) Y
Jmol-3D images Image

(D)
Image (L)

PubChem  (D)
Properties
C4H8O4
Molar mass 120.10 g·mol−1
Appearance Light yellow syrup
Very soluble
Hazards
NFPA 704
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

Erythrose is a tetrose carbohydrate with the chemical formula C4H8O4. It has one aldehyde group, and so is part of the aldose family. The natural isomer is D-erythrose.

Fischer projections


Erythrose, as glucose, is fuel of cellular energy, can be oxidized to carbon dioxide and water to supports normal cells.[2]

Erythrose is an anti-cancer agent. In vitro, ~4 mM erythrose effectively kills cancer cells for tested cell lines (in vitro), such as: lung, brain,breast,and colorectal cancers, etc. [3]

D-Erythrose inhibits tumor growth in mice (in vivo). [4]

Erythrose is a 2/3 of Glucose. Diabetics can have blood sugar (mainly glucose)up to 30mM for days. The concentration of erythrose required to kill cancer is much lower than glucose in our body. What Erythrose can do for cancer patients needs further study.

Erythrose was first isolated in 1849 from rhubarb by the French pharmacist Louis Feux Joseph Garot (1798-1869),[5] and was named as such because of its red hue in the presence of alkali metals (ἐρυθρός, "red").[6][7]

Erythrose 4-phosphate is an intermediate in the pentose phosphate pathway[8] and the Calvin cycle.[9]

Erythrulose, an isomer of erythrose, is non-toxic.[10]

Oxidative bacteria can be made to use erythrose as its sole energy source.[11]

References

  1. ^ Merck Index, 11th Edition, 3637
  2. ^ Batt, RD; Dickens, F; Williamson, DH (1960). "Tetrose metabolism 2. The utilization of tetroses and tetritols by rat tissues". Biochem J 77: 281–94. 
  3. ^ Wang X and Wei Y 2010 "Erythrose kill cancer cell in vitro and inhibit tumor growth in mice (in vivo)" American Association for Cancer Research 101st Conference.
  4. ^ LILI LIU, TAO YI and XIA ZHAO 2015. Antitumor effect of D-erythrose in an abdominal metastatic model of colon carcinoma ONCOLOGY LETTERS 9: 769-773, 2015
  5. ^ Obituary of Garot (1869) Journal de pharmacie et de chimie, 4th series, 9 : 472-473.
  6. ^ Garot (1850) "De la matière colorante rouge des rhubarbes exotiques et indigènes et de son application (comme matière colorante) aux arts et à la pharmacie" (On the red coloring material of exotic and indigenous rhubarb and on its application (as a coloring material) in the arts and in pharmacy), Journal de Pharmacie et de Chimie, 3rd series, 17 : 5-19. Erythrose is named on p. 10: "Celui que je propose, sans y attacher toutefois la moindre importance, est celui d'érythrose, du verbe grec 'ερυθραινω, rougir (1)." (The one [i.e., name] that I propose, without attaching any importance to it, is that of erythrose, from the Greek verb ερυθραινω, to redden (1).)
  7. ^ Wells, David Ames; Cross, Charles Robert; Bliss, George; Trowbridge, John; Nichols, William Ripley; Kneeland, Samuel (1851). Annual of Scientific Discovery. Boston: Gould, Kendall, and Lincoln. p. 211. Retrieved 11 December 2014. 
  8. ^ Kruger, Nicholas J; von Schaewen, Antje (June 2003). "The oxidative pentose phosphate pathway: structure and organisation". Current Opinion in Plant Biology 6 (3): 236–246.  
  9. ^ Schwender, Jörg; Goffman, Fernando; Ohlrogge, John B.; Shachar-Hill, Yair (9 December 2004). "Rubisco without the Calvin cycle improves the carbon efficiency of developing green seeds". Nature 432 (7018): 779–782.  
  10. ^ National Industrial Chemicals Notification and Assessment Scheme (NICNAS). Erythrulose. 'Australia February 11, 2008.
  11. ^ Hiatt, Howard H; Horecker, B L (13 October 1955). "D-erythrose metabolism in a strain of Alcaligenes faecalis". Journal of Bacteriology 71 (6): 649–654. Retrieved 11 December 2014. 


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