Ectoine

Ectoine[1]
Names
	IUPAC name (S)-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid
	Other names Ectoine sodium salt monohydrate; THP(B); RonaCare; Pyrostatin B;
Identifiers
CAS Number	96702-03-3 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:27592 ;
ChemSpider	112069 ;
KEGG	C06231 ;
PubChem CID	126041;
UNII	7GXZ3858RY ;
CompTox Dashboard (EPA)	DTXSID50869280 ;
	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	142.158 g·mol−1
Appearance	White powder
Density	1.568 g/cm3
Solubility in water	Soluble in water
Hazards
NFPA 704 (fire diamond)	[2] 1 1 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	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,[3][4] 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:

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.[6][5]

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.[5]

References

Ectoine at Sigma-Aldrich
Ectoine SDS
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.
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: 129–136. doi:10.1099/00221287-139-1-129.
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.
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.
Augenstein, Seth (2016-09-06). "'Extremophile Bacteria' Will Eat Away Wreck of the Titanic". laboratoryequipment.com.
Zaccai, Giuseppe; Bagyan, Irina; Combet, Jérôme; Cuello, Gabriel J.; Demé, Bruno; Fichou, Yann; Gallat, François-Xavier; Galvan Josa, Victor M.; von Gronau, Susanne; Haertlein, Michael; Martel, Anne; Moulin, Martine; Neumann, Markus; Weik, Martin; Oesterhelt, Dieter (16 August 2016). "Neutrons describe ectoine effects on water H-bonding and hydration around a soluble protein and a cell membrane". Scientific Reports. 6: 31434. Bibcode:2016NatSR...631434Z. doi:10.1038/srep31434. PMC 4985633. PMID 27527336.
"HAMAP: Halorhodospira halophila (strain DSM 244 / SL1) (Ectothiorhodospira halophila (strain DSM 244 / SL1)) complete proteome ExPASy Proteomics Server. Swiss Institute of Bioinformatics http://hamap.expasy.org/proteomes/HALHL.html
Zhu, Daochen; Niu, Lili; Wang, Chenxiang; Nagata, Shinichi (September 2007). "Isolation and characterisation of moderately halophilic bacteriumHalomonas ventosae DL7 synthesizing ectoine as compatible solute" (PDF). Annals of Microbiology. 57 (3): 401–406. doi:10.1007/BF03175080.

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[1] Ectoine at Sigma-Aldrich

[2] Ectoine SDS

[r2-3] 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.

[r1-4] 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: 129–136. doi:10.1099/00221287-139-1-129.

[r4-5] 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.

[r3-6] 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.

[7] Augenstein, Seth (2016-09-06). "'Extremophile Bacteria' Will Eat Away Wreck of the Titanic". laboratoryequipment.com.

[8] Zaccai, Giuseppe; Bagyan, Irina; Combet, Jérôme; Cuello, Gabriel J.; Demé, Bruno; Fichou, Yann; Gallat, François-Xavier; Galvan Josa, Victor M.; von Gronau, Susanne; Haertlein, Michael; Martel, Anne; Moulin, Martine; Neumann, Markus; Weik, Martin; Oesterhelt, Dieter (16 August 2016). "Neutrons describe ectoine effects on water H-bonding and hydration around a soluble protein and a cell membrane". Scientific Reports. 6: 31434. Bibcode:2016NatSR...631434Z. doi:10.1038/srep31434. PMC 4985633. PMID 27527336.

[9] "HAMAP: Halorhodospira halophila (strain DSM 244 / SL1) (Ectothiorhodospira halophila (strain DSM 244 / SL1)) complete proteome ExPASy Proteomics Server. Swiss Institute of Bioinformatics http://hamap.expasy.org/proteomes/HALHL.html

[10] Zhu, Daochen; Niu, Lili; Wang, Chenxiang; Nagata, Shinichi (September 2007). "Isolation and characterisation of moderately halophilic bacteriumHalomonas ventosae DL7 synthesizing ectoine as compatible solute" (PDF). Annals of Microbiology. 57 (3): 401–406. doi:10.1007/BF03175080.