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EntityQ414414· pop 18· linked from 16 articles

Also known as (+)-1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid, L-ectoine

Ectoine (3,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) is a natural compound found in several species of bacteria. It is a compatible solute which serves as a protective substance by acting as an osmolyte and thus helps organisms survive extreme osmotic stress. Furthermore it was shown to protect DNA against ionizing and ultraviolet radiation serving as a radical scavenger. Ectoine is found in high concentrations in halophilic microorganisms and confers resistance towards salt and temperature stress. Ectoine was first identified in the microorganism Ectothiorhodospira halochloris, b

Wikidata facts

Mass
142.074
Show 4 more facts
chemical formula
C₆H₁₀N₂O₂
canonical SMILES
CC1=NCCC(N1)C(=O)O
isomeric SMILES
CC1=NCC[C@H](N1)C(=O)O
Commons category
Ectoine
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Article

4 sections
Contents
  • Biosynthesis
  • Use in cosmetics
  • Medical use
  • References

Ectoine (3,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) is a natural compound found in several species of bacteria. It is a compatible solute which serves as a protective substance by acting as an osmolyte and thus helps organisms survive extreme osmotic stress. Furthermore it was shown to protect DNA against ionizing and ultraviolet radiation serving as a radical scavenger. Ectoine is found in high concentrations in halophilic microorganisms and confers resistance towards salt and temperature stress. Ectoine was first identified in the microorganism Ectothiorhodospira halochloris, but has since been found in a wide range of Gram-negative and Gram-positive bacteria. Other species of bacteria in which ectoine was found include: Brevibacterium linens Halomonas elongata Marinococcus halophilus Pseudomonas stutzeri Halomonas titanicae Halorhodospira halophila Halomonas ventosae

== Biosynthesis == Ectoine is synthesized in three successive enzymatic reactions starting from aspartic β-semialdehyde. The genes involved in the biosynthesis are called ectA, ectB and ectC, and they encode the enzymes L-2,4-diaminobutyric acid acetyltransferase, L-2,4-diaminobutyric acid transaminase and L-ectoine synthase, respectively.

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