4433-40-3

Hydroxymethyl uracil is a product of oxidative damage to DNA, predominantly by hydroxyl radical via the Fenton reaction.

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5-Hydroxymethyluracil (cas# 4433-40-3) is a compound useful in organic synthesis.

ChEBI: A primary alcohol that is uracil bearing a hydroxymethyl substituent at the 5-position.

5-Hydroxymethyluracil is produced by the enzyme thymine dioxygenase (EC 1.14.11.6) which catalyzes the chemical reaction thymine + 2-oxoglutarate + O2 <-> 5-hydroxymethyluracil + succinate + CO2.
The 3 substrates of this enzyme are thymine, 2-oxoglutarate, and O2, whereas its 3 products are 5-hydroxymethyluracil, succinate, and CO2. The 5hmU base can also be generated by oxidation/hydroxylation of thymine by the Ten-Eleven-Translocation (TET) proteins or result from deamination of 5hmC. DNA containing 5hmU has been reported to be more flexible and hydrophilic.

5-Hydroxymethyluracil (5hmU) is a thymine base modification found in the genomic DNA of diverse organisms ranging from bacteriophages to mammals.

[1] Patent: US2004/38995, 2004, A1. Location in patent: Page/Page column 4-6
[2] Synlett, 2002, # 12, p. 2043 - 2044
[3] Patent: US2016/75720, 2016, A1. Location in patent: Paragraph 0321
[4] Canadian Journal of Chemistry, 2007, vol. 85, # 4, p. 302 - 312
[5] Canadian Journal of Chemistry, 2005, vol. 83, # 10, p. 1731 - 1740