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Isolation and chemical conversion of two novel prostaglandin endoperoxides: 5(6)‐epoxy‐PGG 1 and 5(6)‐epoxy‐PGH 1
Author(s) -
Oliw Ernst H.
Publication year - 1984
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(84)81141-2
Subject(s) - epoxy , chemistry , phenol , silicic acid , incubation , bisphenol a , polymer chemistry , nuclear chemistry , organic chemistry , biochemistry
5(6)‐Epoxy‐PGG 1 and 5(6)‐epoxy‐PGH 1 were isolated after incubation of microsomes of RSV with 3 H‐labelled 5(6)‐epoxy‐C20:3 for 45 s at 37°C. The endoperoxides were methylated and characterized by conversion to prostaglandins. In buffer, the endoperoxides were converted to methyl‐5(6)‐epoxy‐PGE 1 and methyl‐5(6)‐epoxy‐15‐hydroperoxy‐PGE 1 , while treatment with SnCl 2 reduced the endoperoxides to methyl‐5‐hydroxy‐PGI 1α and methyl‐5‐hydroxy‐PGI 1β . Significant amounts of methyl‐5(6)‐epoxy‐HHD were also formed. The endoperoxides could be separated by silicic acid chromatography and when 1 mM phenol was present in the incubation, 5(6)‐epoxy‐PGH 1 was obtained as the main product.