Ectoine

Ectoine^[1]

Names
IUPAC name (S)-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid
Other names THP(B)
Identifiers
CAS Number	96702-03-3
ChEBI	CHEBI:27592
ChemSpider	112069
Jmol interactive 3D	Image Image
KEGG	C06231
PubChem	126041
UNII	7GXZ3858RY
InChI InChI=1S/C6H10N2O2/c1-4-7-3-2-5(8-4)6(9)10/h5H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m0/s1 Key: WQXNXVUDBPYKBA-YFKPBYRVSA-N InChI=1/C6H10N2O2/c1-4-7-3-2-5(8-4)6(9)10/h5H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m0/s1 Key: WQXNXVUDBPYKBA-YFKPBYRVBN
SMILES CC1=NCCC(N1)C(=O)O O=C(O)[C@H]1N\C(=N/CC1)C
Properties
Chemical formula	C6H10N2O2
Molar mass	142.16 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Ectoine (1,4,5,6-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. 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,^[2][3] but has since been found in a wide range of Gram-negative and Gram-positive bacteria. Other species of ectoine were found in

• Brevibacterium linens^[3]
• Halomonas elongata^[2][4]
• Marinococcus halophilus^[5]
• Pseudomonas stutzeri^[4]

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.^[5][4]

Use

Ectoine is used as an active ingredient in skin care and sun protection products. It stabilizes proteins and other cellular structures and protects the skin from stresses like UV irradiation and dryness.^[4]

References

1. Ectoine at Sigma-Aldrich
2. Peters, P; Miwatani, T; Honda, T (1990). "The biosynthesis of ectoine". FEMS Microbiology Letters 71 (2): 157–61. doi:10.1016/0378-1097(90)90049-V. PMID 1601286.
3. Bernard, T.; Jebbar, M.; Rassouli, Y.; Himdi-Kabbab, S.; Hamelin, J.; Blanco, C. (1993). "Ectoine accumulation and osmotic regulation in Brevibacterium linens" (PDF). Journal of General Microbiology 139: 129. doi:10.1099/00221287-139-1-129.
4. Stöveken, N; Pittelkow, M; Sinner, T; Jensen, R. A.; Heider, J; Bremer, E (2011). "A specialized aspartokinase enhances the biosynthesis of the osmoprotectants ectoine and hydroxyectoine in Pseudomonas stutzeri A1501". Journal of Bacteriology 193 (17): 4456–68. doi:10.1128/JB.00345-11. PMC 3165526. PMID 21725014.
5. Louis, P; Galinski, E. A. (1997). "Characterization of genes for the biosynthesis of the compatible solute ectoine from Marinococcus halophilus and osmoregulated expression in Escherichia coli". Microbiology. 143 ( Pt 4) (4): 1141–9. doi:10.1099/00221287-143-4-1141. PMID 9141677.