H. Sprecher, S. Sankarappa
1982
Citations
0
Influential Citations
29
Citations
Journal
Methods in Enzymology
Abstract
Publisher Summary This chapter discusses the synthesis of radiolabeled fatty acids. The synthesis can be divided into five steps: (1) preparation of 6-heptyn-l-ol, (2) synthesis of 1-bromo-2,5,8,11-tetradecatetrayne, (3) coupling of these two intermediates to give heneicosa-6,9,12,15,18-pentayn- l-ol, (4) reduction of this acetylenic alcohol to the ethylenic analog and subsequent purification of heneicosa-6,9,12,15,18-pentaen-l-ol, and (5) conversion of this alcohol to 7,10,13,16,19-[ 1- 14 C] docosapentaenoic acid. Even though the alcohol used for the synthesis of a 1- 14 C-labeled acids contains no detectable contaminants, small amounts of radioactive impurities are found when the methyl esters of radioactive fatty acids were analyzed by argentation or high-performance liquid chromatography. The methyl ester is then again purified by argentation thin layer chromatography. Although the presentation is confined to the methods used for the preparation of this acid, this general procedure can be used for the synthesis of any all- cis acid that contains the skipped (methylene interrupted) pattern of unsaturation.