Ectoine

Catalog	BBC96702033
CAS	96702-03-3
Structure
Description	4-pyrimidincarbonsure (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. 4-pyrimidincarbonsure is found in high concentrations in halophilic microorganisms and confers resistance towards salt and temperature stress. 4-pyrimidincarbonsure 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 4-pyrimidincarbonsure were found in
Synonyms	(S)-1,4,5,6-Tetrahydro-2-methyl-4-pyrimidincarbonsure
IUPAC Name	(6S)-2-methyl-1,4,5,6-tetrahydropyrimidine-6-carboxylic acid
Molecular Weight	142.16
Molecular Formula	C6H10N2O2
Canonical SMILES	CC1=NCC[C@H](N1)C(=O)O
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
InChI Key	WQXNXVUDBPYKBA-YFKPBYRVSA-N
Melting Point	280 °C
Flash Point	184.5ºC
Purity	98%
Density	1.37 g/ml
Appearance	White powder
pH	6-8
pKa	3.14±0.20
Refractive Index	1.596

Case Study

Therapeutic Potential of Ectoine as A Promising Protective Agent in Human and Animals

Bownik A, et al. Arhiv za higijenu rada i toksikologiju, 2016, 67(4), 260-264.

Many biophysical studies have shown that ectoine binds to water molecules even better than some other osmoprotectants such as glycerol. Ectoine exhibits therapeutic potential in multiple aspects in humans and animals.
· Skin Protection: Ectoine has been widely used in cosmetic anti-aging and moisturizers to improve the skin's tolerance to surfactants in skin cleansing solutions. Ectoine is also an effective long-lasting moisturizer and can strongly absorbs ultraviolet (UV) radiation.
· Stabilizes enzyme activity: Ectoine increases the stability of enzymes that maintain hydration, thereby reducing the susceptibility to protein denaturation.
· Cell protection: Ectoine may protect cells from various environmental stressors in a variety of ways, such as increasing cell membrane fluidity and improving cell surface hydration.
· Reduce inflammatory response: Tetrahydromethylpyrimidine can effectively reduce inflammation. For example, nasal sprays and air drops containing ectoine are effective treatments for allergic rhinitis, rhinoconjunctivitis, and dry eye syndrome.
· Cryoprotection: Compatible solutes such as ectoine and hydroxyectoine are effective reagents for cryopreservation.
· Preventing Neurodegenerative Diseases: Ectoine has been found to prevent amyloid formation and delay the onset and progression of Alzheimer's disease.

Biosynthetic Pathway and Transformation of Ectoine

Kunte H J, et al. Current Biotechnology, 2014, 3(1), 10-25.

Ectoine is produced industrially through biotechnological processes using the halophilic γ-proteobacterium H. elongata. Ectoine is synthesized from aspartate semialdehyde, and its formation involves three enzymatic steps. In addition, ectoine can be further converted into 5-hydroxyectoine under the action of ectoine hydroxylase.
· Initially, aspartate-semialdehyde is transaminated to 2,4-diaminobutyric acid (DABA) using glutamate as the amino-group donor, catalyzed by DABA transaminase EctB. Gel filtration tests with purified protein from H. elongata suggest that DABA aminotransferase EctB may form a homohexamer in its natural state.
· Subsequently, DABA-Nγ-acetyltransferase EctA transfers an acetyl group from acetyl-CoA to DABA to produce Nγ-acetyl-L-2,4-diaminobutyric acid.
· Lastly, EctC, an ectoine synthase, facilitates the cyclic condensation of Nγ-acetyl-2,4-diaminobutyric acid to produce ectoine. Belonging to the enzyme family of carbon-oxygen lyases, in vitro tests with purified EctC demonstrate that its ectoine-synthase activity and substrate affinity are significantly impacted by NaCl.
· Under certain stress conditions (e.g. elevated temperatures) H. elongata converts some of the ectoine to 5- hydroxyectoine by ectoine hydroxylase (EctD) catalysis.