Ectoine[ 1]
Names
Preferred IUPAC name
(4S )-2-Methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid
Other names
Ectoine sodium salt monohydrate
THP(B)
RonaCare
Pyrostatin B
Identifiers
ChEBI
ChemSpider
KEGG
UNII
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
Y Key: WQXNXVUDBPYKBA-YFKPBYRVSA-N
Y 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
CC1=NCCC(N1)C(=O)O
O=C(O)[C@H]1N\C(=N/CC1)C
Properties
C 6 H 10 N 2 O 2
Molar mass
142.158 g·mol−1
Appearance
White powder
Density
1.568 g/cm3
Soluble in water
Hazards
NFPA 704 (fire diamond)
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
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:
^ Ectoine at Sigma-Aldrich
^ Ectoine SDS
^ a b 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 .
^ a b 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 .
^ a b 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 (6 September 2016). " '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 [permanent dead link ] 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 . S2CID 43421438 . Archived from the original (PDF) on 2 October 2020. Retrieved 5 December 2019 .