12-Hydroxy-5,8,10 heptadecatrienoic acid → Prostaglandin D2

HRID 1865763

Reaktionsgleichung

Reaktionsgleichung von HRID 1865763
C(#N)C.[CH3:4][CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]([OH:33])/[CH:10]=[CH:11]/[C@@H:12]1[C@@H:16]([CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][C:23]([O:25]CC(O)CO)=[O:24])[C@H:15]2[O:31][O:32][C@@H:13]1[CH2:14]2.OC(CCCCC)C=CC=CCC=CCCCC(O)=O>O.CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(OC(CO)CO)=O>[CH3:4][CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]([OH:33])/[CH:10]=[CH:11]/[C@@H:12]1[C@@H:16]([CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[C:15](=[O:31])[CH2:14][C@H:13]1[OH:32].[CH3:4][CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]([OH:33])/[CH:10]=[CH:11]/[C@H:12]1[C:13](=[O:32])[CH2:14][C@H:15]([OH:31])[C@@H:16]1[CH2:17]/[CH:18]=[CH:19]\[CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24]

Komponenten

7

Edukt 3

HCID 141412-Hydroxy-5,8,10 heptadecatrienoic acidHCID 6342AcetonitrileHCID 247784921(3)-glyceryl-PGH2

Produkt 2

HCID 448457Prostaglandin D2HCID 5280360Prostaglandin E2

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 52822802-ArachidonylglycerolLösungsmittel2×

Versuchsvorschrift

In general, COX-2 enzymatic products can be detected or measured by a variety of methods. For example, reversed phase liquid chromatography-mass spectrometry is used to detect or measure COX-2 enzymatic produces. FIG. 12 is a selected-ion mass chromatogram of oxygenated 2-AG metabolites with (a) m/z=449.3 and (b) m/z=417.3 (Kozak et al. 2000, supra). For example, products are eluted with a 15-minute gradient of 20% to 100% acetonitrile in H2O (0.001% sodium acetate). LC/MS reveals the presence of five primary products in 2-AG/COX-2 reaction mixtures. Two closely eluting polar products each display m/z 449 consistent with the non-enzymatic PGH2-G isomerization products PGE2-G and PGD2-G (FIG. 12). Pentadeuterated standards of glyceryl esters of PGE2 and PGD2 are synthesized and coelute with these two polar products under multiple chromatographic conditions. An intermediate polarity product with m/z 377 is observed that is consistent with the PGH2-G degradation product 12-hydroxyheptadeca-5,8,10-trienoic acid (HHT-G, data not shown). Finally, two closely eluting non-polar 2-AG metabolites are detected with an m/z of 417, consistent with the glyceryl esters of HETEs (hydroxyeicosatetraenoic acids that are minor products of arachidonic acid oxygenation by COX-2) (FIG. 12).

Aufarbeitung

  1. customare eluted with a 15-minute
  2. customreaction mixtures
  3. washTwo closely eluting polar products each display m/z 449 consistent with the non-enzymatic PGH2-G
  4. washFinally, two closely eluting non-polar 2-AG metabolites
  5. customare detected with an m/z of 417, consistent with the glyceryl esters of HETEs (hydroxyeicosatetraenoic acids that are minor products of arachidonic acid oxygenation by COX-2) (FIG. 12)

Quellen und Nachweise

ORD-Eintrag
ord-b3831fab31534c49a153fc11fb6785ea
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07628975B2

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