Biosynthesis of ansatrienin by Streptomyces collinus: cell-free transformations of cyclohexene- and cyclohexadienecarboxylic acids.
Cell-free extracts of Streptomyces collinus were tested with various cyclohexene- and cyclohexadienecarboxylic acids in order to determine the latter stages of the conversion of shikimic acid to cyclohexanecarboxylic acid. It was demonstrated that the final three steps of this process involve reduction of the alpha,beta-double bond of 1(6),2-cyclohexadienylcarbonyl CoA, an isomerization of the double bond of the resulting 2-cyclohexenylcarbonyl CoA to afford 1-cyclohexenylcarbonyl CoA, and a subsequent reduction of the newly formed alpha,beta-double bond. Both of the reduction steps were shown to require NADPH as a cofactor.
Reynolds
K A
KA
Department of Biomedicinal Chemistry, University of Maryland, Baltimore 21201.
Wang
P
P
Fox
K M
KM
Floss
H G
HG
D000900:Anti-Bacterial Agents / Q000096:biosynthesis*; D002264:Carboxylic Acids / Q000378:metabolism; D002474:Cell-Free System; D003510:Cyclohexanes / Q000378:metabolism; D053138:Cyclohexenes; D011809:Quinones / Q000378:metabolism; D013302:Streptomyces / Q000378:metabolism*
D000900:Anti-Bacterial Agents; D002264:Carboxylic Acids; D003510:Cyclohexanes; D053138:Cyclohexenes; D011809:Quinones; C052568:cyclohexene; C036970:mycotrienin I