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|ImageFile=Levuglandin D2.svg |
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|IUPACName=(5''Z'',8''R'',9''R'',10''E'',12''S'')-9-acetyl-8-formyl-12- hydroxyheptadeca-5,10-dienoic acid |
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|Name=Levuglandin D<sub>2</sub> |
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| ImageFile=Levuglandin D2.svg |
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| IUPACName=(5''Z'',8''R'',9''R'',10''E'',12''S'')-9-acetyl-8-formyl-12- hydroxyheptadeca-5,10-dienoic acid |
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|Section1= {{Chembox Identifiers |
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| Name=Levuglandin D<sub>2</sub> |
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| CASNo=91712-44-6 |
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| PubChem=9548876 |
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|Section1={{Chembox Identifiers |
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| SMILES=CCCCCC(C=CC(C(CC=CCCCC(=O)O)C=O)C(=O)C)O |
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| CASNo_Ref = {{cascite|correct|??}} |
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| KEGG=C13808 |
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| CASNo=91712-44-6 |
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| PubChem=9548876 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 7827799 |
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| SMILES = CCCCC(/C=C/((C/C=C\CCCC(=O)O)C=O)C(=O)C)O |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C20H32O5/c1-3-4-7-11-18(23)13-14-19(16(2)22)17(15-21)10-8-5-6-9-12-20(24)25/h5,8,13-15,17-19,23H,3-4,6-7,9-12H2,1-2H3,(H,24,25)/b8-5-,14-13+/t17-,18-,19-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = MLLWPVVMXGUOHD-QNUMDXCLSA-N |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG=C13808 |
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|Section2= {{Chembox Properties |
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| Formula=C<sub>20</sub>H<sub>32</sub>O<sub>5</sub> |
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| Formula=C<sub>20</sub>H<sub>32</sub>O<sub>5</sub> |
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| MolarMass=352.465 g/mol |
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| MolarMass=352.465 g/mol |
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|ImageFile=Levuglandin E2.svg |
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|IUPACName=(5''Z'',8''R'',9''R'',10''E'',12''S'')-8-acetyl-9-formyl-12- hydroxyheptadeca-5,10-dienoic acid |
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| IUPACName=(5''Z'',8''R'',9''R'',10''E'',12''S'')-8-acetyl-9-formyl-12- hydroxyheptadeca-5,10-dienoic acid |
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|Name=Levuglandin E<sub>2</sub> |
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| Name=Levuglandin E<sub>2</sub> |
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|OtherNames= LGE2 |
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| OtherNames= LGE2 |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo=91712-41-3 |
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| CASNo=91712-41-3 |
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| PubChem=5771742 |
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| PubChem=5771742 |
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| ChemSpiderID = 4696839 |
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| SMILES=CCCCCC(C=CC(C=O)C(CC=CCCCC(=O)O)C(=O)C)O |
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| SMILES = CCCCC(/C=C/(C=O)(C/C=C\CCCC(=O)O)C(=O)C)O |
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| KEGG=C13807 |
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| StdInChI = 1S/C20H32O5/c1-3-4-7-10-18(23)14-13-17(15-21)19(16(2)22)11-8-5-6-9-12-20(24)25/h5,8,13-15,17-19,23H,3-4,6-7,9-12H2,1-2H3,(H,24,25)/b8-5-,14-13+/t17-,18-,19-/m0/s1 |
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| StdInChIKey = WJWAORNTZNRHBP-QNUMDXCLSA-N |
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| KEGG=C13807 |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>20</sub>H<sub>32</sub>O<sub>5</sub> |
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| Formula=C<sub>20</sub>H<sub>32</sub>O<sub>5</sub> |
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| MolarMass=352.465 g/mol |
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| MolarMass=352.465 g/mol |
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'''Levuglandins''' are reactive ]s formed by the spontaneous rearrangement of ] (PGH). Enantiomerically pure levuglandin (LG) E<sub>2</sub> can also be formed through the cyclooxygenase (COX) pathway by a rearrangement of the prostaglandin (PG) endoperoxide PGH <sub>2</sub>.<ref name="pmid16037255">{{cite journal |author=Salomon RG |title=Isolevuglandins, oxidatively truncated phospholipids, and atherosclerosis |journal=Ann. N. Y. Acad. Sci. |volume=1043 |issue= |pages=327–42 |year=2005 |pmid=16037255 |doi=10.1196/annals.1333.040 |url=http://www.annalsnyas.org/cgi/pmidlookup?view=long&pmid=16037255 |accessdate=2008-01-16}}</ref> They are ]s. One species, levuglandin E<sub>2</sub>, (LGE<sub>2</sub>), forms neurotoxic ]s with |
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'''Levuglandins''' are reactive ]s formed by the spontaneous rearrangement of ] (PGH). Enantiomerically pure levuglandin (LG) E<sub>2</sub> can also be formed through the cyclooxygenase (COX) pathway by a rearrangement of the prostaglandin (PG) endoperoxide PGH <sub>2</sub>.<ref name="pmid16037255">{{cite journal |author=Salomon RG |title=Isolevuglandins, oxidatively truncated phospholipids, and atherosclerosis |journal=Ann. N. Y. Acad. Sci. |volume=1043 |pages=327–42 |year=2005 |issue=1 |pmid=16037255 |doi=10.1196/annals.1333.040|bibcode=2005NYASA1043..327S |s2cid=12782911 }}</ref> They are ]s. One species, levuglandin E<sub>2</sub>, (LGE<sub>2</sub>), forms neurotoxic ]s with |
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].<ref name=boutand>{{cite journal |
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].<ref>{{cite journal |
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|doi = 10.1111/j.1471-4159.2005.03586.x|title = PGH2-derived levuglandin adducts increase the neurotoxicity of amyloid beta1-42|year = 2006|last1 = Boutaud|first1 = Olivier|last2 = Montine|first2 = Thomas J.|last3 = Chang|first3 = Lei|last4 = Klein|first4 = William L.|last5 = Oates|first5 = John A.|journal = Journal of Neurochemistry|volume = 96|issue = 4|pages = 917–923|pmid = 16412101|pmc = 1621054}}</ref><ref>{{cite journal|doi=10.1021/bi990470+|pmid=10413514|year=1999|last1=Boutaud|first1=O.|last2=Brame|first2=C. J.|last3=Salomon|first3=R. G.|last4=Roberts Lj|first4=2nd|last5=Oates|first5=J. A.|title=Characterization of the lysyl adducts formed from prostaglandin H2 via the levuglandin pathway|journal=Biochemistry|volume=38|issue=29|pages=9389–96}}</ref> |
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|author= Bautaud ''et al.'' |
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|format=pdf |
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|url= http://www.blackwell-synergy.com/doi/pdf/10.1111/j.1471-4159.2005.03586.x |
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|journal= Biochemistry |volume=38|pages=9389–9396 |
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|title = PGH -derived levuglandin adducts increase the neurotoxicity of Amyloid Β<sub>1–42</sub> |
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|accessdate=2007-10-02 |
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|doi = 10.1021/bi990470 |
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|year = 1999 |
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|pmid= 10413514 |
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|last2= Brame |
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|first2= CJ |
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|last3= Salomon |
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|first3= RG |
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|last4= Roberts Lj |
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|first4= 2nd |
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|last5= Oates |
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|first5= JA |
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|issue= 29}}</ref> |
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Levuglandins and isolevuglandins can damage proteins by covalent adduction, thereby interfering with their normal functions. |
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Levuglandins and isolevuglandins can damage proteins by covalent adduction, thereby interfering with their normal functions. |
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These lipid-derived protein modifications may serve as dosimeters of oxidative injury. |
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These lipid-derived protein modifications may serve as dosimeters of oxidative injury. |
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==History== |
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==History== |
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Though spontaneous rearrangements of PGH2 are known to generate prostaglandins (PG) PGD2 and PGE2.<ref>M. Hamberg and B. Samuelsson, Detection and isolation of an endoperoxide intermediate in prostaglandin biosynthesis, Proc. Natl. Acad. Sci. U.S.A. 70 (1973), pp. 899–903.</ref><ref>D.H. Nugteren and E. Hazelhof, Isolation and properties of intermediates in prostaglandin biosynthesis, Biochim. Biophys. Acta 326 (1973) (3), pp. 448–461.</ref> Prof. Robert Salomon at Case Western Reserve University discovered that a novel alternative rearrangement also occurs that producing two γ-ketoaldehydes<ref>R.G. Salomon, D.B. Miller, M.G. Zagorski and D.J. Coughlin, Prostaglandin endoperoxides. 14. Solvent-induced fragmentation of prostaglandin endoperoxides. New aldehyde products from PGH2 and a novel intramolecular 1*2-hydride shift during endoperoxide fragmentation in aqueous solution, J. Am. Chem. Soc. 106 (1984) (20), pp. 6049–6060.</ref> and named them levuglandins LGD2 and LGE2 as they are derivatives of levulinaldehyde with prostanoid side chains. |
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Though spontaneous rearrangements of PGH2 are known to generate prostaglandins (PG) PGD2 and PGE2.<ref>{{cite journal | author = Hamberg M., Samuelsson B. | year = 1973 | title = Detection and isolation of an endoperoxide intermediate in prostaglandin biosynthesis | journal = Proc. Natl. Acad. Sci. U.S.A. | volume = 70 | issue = 3| pages = 899–903 | doi=10.1073/pnas.70.3.899| pmc = 433384 | pmid=4514999| bibcode = 1973PNAS...70..899H | doi-access = free }}</ref><ref>{{cite journal | author = Nugteren D.H., Hazelhof E. | year = 1973 | title = Isolation and properties of intermediates in prostaglandin biosynthesis | journal = Biochim. Biophys. Acta | volume = 326 | issue = 3| pages = 448–461 | doi=10.1016/0005-2760(73)90145-8| pmid = 4776443 }}</ref> Prof. Robert Salomon at Case Western Reserve University discovered that a novel alternative rearrangement also occurs that producing two γ-ketoaldehydes<ref>{{cite journal |author1=Salomon R.G. |author2=Miller D.B. |author3=Zagorski M.G. |author4=Coughlin D.J. | year = 1984 | title = Prostaglandin endoperoxides. 14. Solvent-induced fragmentation of prostaglandin endoperoxides. New aldehyde products from PGH2 and a novel intramolecular 1*2-hydride shift during endoperoxide fragmentation in aqueous solution | journal = J. Am. Chem. Soc. | volume = 106 | issue = 20| pages = 6049–6060 | doi=10.1021/ja00332a049}}</ref> and named them levuglandins LGD2 and LGE2 as they are derivatives of levulinaldehyde with prostanoid side chains. |
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==References== |
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==References== |