| 词条 | Ectoine |
| 释义 |
| Watchedfields = changed | verifiedrevid = 443720196 | Reference=[1] | ImageFile=Ectoine structural formulae v.1.png | ImageSize=120px | IUPACName=(S)-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid | OtherNames=THP(B) |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 112069 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C06231 | 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 | InChIKey = WQXNXVUDBPYKBA-YFKPBYRVBN | SMILES1 = O=C(O)[C@H]1N\\C(=N/CC1)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = WQXNXVUDBPYKBA-YFKPBYRVSA-N | CASNo_Ref = {{cascite|correct|??}} | CASNo=96702-03-3 | PubChem=126041 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 7GXZ3858RY | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 27592 | SMILES=CC1=NCCC(N1)C(=O)O |Section2={{Chembox Properties | C=6 | H=10 | N=2 | O=2 | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }} 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 bacteria in which ectoine was found include
BiosynthesisEctoine 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.[4][5] UseEctoine 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] References1. ^Ectoine at Sigma-Aldrich 2. ^1 {{cite journal|doi=10.1099/00221287-139-1-129|url=http://www.microbiologyresearch.org/docserver/fulltext/micro/139/1/mic-139-1-129.pdf|title=Ectoine accumulation and osmotic regulation in Brevibacterium linens|journal=Journal of General Microbiology|volume=139|pages=129-136|year=1993|last1=Bernard|first1=T.|last2=Jebbar|first2=M.|last3=Rassouli|first3=Y.|last4=Himdi-Kabbab|first4=S.|last5=Hamelin|first5=J.|last6=Blanco|first6=C.}} 3. ^1 {{cite journal|doi=10.1016/0378-1097(90)90049-V |pmid=1601286 |title=The biosynthesis of ectoine |journal=FEMS Microbiology Letters |volume=71 |issue=2 |pages=157–61 |year=1990 |last1=Peters |first1=P |last2=Miwatani |first2=T |last3=Honda |first3=T }} 4. ^1 {{cite journal|pmid=9141677|year=1997|author1=Louis|first1=P|title=Characterization of genes for the biosynthesis of the compatible solute ectoine from Marinococcus halophilus and osmoregulated expression in Escherichia coli|journal=Microbiology|volume=143 ( Pt 4)|issue=4|pages=1141–9|last2=Galinski|first2=E. A.|doi=10.1099/00221287-143-4-1141}} 5. ^1 2 3 {{cite journal|pmid=21725014|pmc=3165526|year=2011|author1=Stöveken|first1=N|title=A specialized aspartokinase enhances the biosynthesis of the osmoprotectants ectoine and hydroxyectoine in Pseudomonas stutzeri A1501|journal=Journal of Bacteriology|volume=193|issue=17|pages=4456–68|last2=Pittelkow|first2=M|last3=Sinner|first3=T|last4=Jensen|first4=R. A.|last5=Heider|first5=J|last6=Bremer|first6=E|doi=10.1128/JB.00345-11}} 6. ^{{cite web|last1=Augenstein|first1=Seth|title='Extremophile Bacteria' Will Eat Away Wreck of the Titanic|url=http://www.laboratoryequipment.com/news/2016/09/extremophile-bacteria-will-eat-away-wreck-titanic-2030|website=laboratoryequipment.com|date=2016-09-06}} 7. ^{{cite journal|last1=Zaccai|first1=Giuseppe|last2=Bagyan|first2=Irina|last3=Combet|first3=Jérôme|last4=Cuello|first4=Gabriel J.|last5=Demé|first5=Bruno|last6=Fichou|first6=Yann|last7=Gallat|first7=François-Xavier|last8=Galvan Josa|first8=Victor M.|last9=von Gronau|first9=Susanne|last10=Haertlein|first10=Michael|last11=Martel|first11=Anne|last12=Moulin|first12=Martine|last13=Neumann|first13=Markus|last14=Weik|first14=Martin|last15=Oesterhelt|first15=Dieter|title=Neutrons describe ectoine effects on water H-bonding and hydration around a soluble protein and a cell membrane|journal=Scientific Reports|date=16 August 2016|volume=6|pages=31434|doi=10.1038/srep31434|pmid=27527336|pmc=4985633}} 8. ^"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 9. ^{{cite journal|last1=Zhu|first1=Daochen|last2=Niu|first2=Lili|last3=Wang|first3=Chenxiang|last4=Nagata|first4=Shinichi|title=Isolation and characterisation of moderately halophilic bacteriumHalomonas ventosae DL7 synthesizing ectoine as compatible solute|journal=Annals of Microbiology|date=September 2007|volume=57|issue=3|pages=401–406|doi=10.1007/BF03175080}} 2 : Amidines|Carboxylic acids |
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