The base promoted oligomerization of 15-dehydro-prostaglandin B1: dimer formation and structural implications for a complex mixture termed PGBx

✍ Scribed by George L. Nelson; Gregory L. Verdine

• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 323 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)81584-1

✦ Synopsis

The base promoted oligomerization of 15-dehydro-PGB1_ (la) results in the formation of six dimers via a Michael addition pathway. The simultaneous operation of multiple reaction sites as required by dimer formation has major consequences for the structural complexity of the oligomeric mixture PGBx. Recently we reported the isolation end characterization of six dimers from the oligomeric mixture formed upon treatment of the 15-dehydro-PGBi analog Ic with dilute ethsnolic KOH. The oligomerization pathway leading to dimer formation, which proceeded via Michael addition through multiple reaction sites, provided for the first time structural insights into the complex mixture termed PGBx. The term PGBx currently refers to a complex mixture derived from treatment of i5dehydro-PGa methyl ester (lb) with I N ethenolic KOH for 4 hours at 800.* PGBx has been reported to protect against the loss of oxidative phosphorylation in vitro in isolated mitochondria3 end -reverse in vivo damage in animals subjected to episodes of myocardial3b and cerebraljc ischemia. --Recently Toda et, al.4 reported the formation of two dimers from the prolonged base treatment of PGBi, en earlier precursor of a complex mixture also termed PGBx,* that are markedly different in structure from the six dimers derived from the l5-dehydro-PGBI analog lc. Two diners have also been reported by Polis et. al.5 from the treatment of 15-dehydro-PGB1 methyl ester @)