| Title: | Efficient generation of a trisporoid library by combination of synthesis and biotransformation |
| Author(s): | Schachtschabel D; Boland W; |
| Address: | "Department of Bioorganic Chemistry, Max-Planck-Institute for Chemical Ecology, Hans-Knoll-Strasse 8, D-07745 Jena, Germany" |
| ISSN/ISBN: | 0022-3263 (Print) 0022-3263 (Linking) |
| Abstract: | "Trisporic acids and their biosynthetic precursors represent a family of powerful fungal pheromones and morphogenetic factors. A highly flexible synthetic protocol is described that (i) provides rapid access to nonfunctionalized early trisporoids from beta-ionone, (ii) includes a regiospecific oxidative functionalization of beta-ionone leading to 1-acetoxy-beta-ionone giving access to functionalized trisporoids, and (iii) utilizes a biotransformation of early synthetic trisporoids by growing cells of Blakeslea trispora to prepare late trisporoids including trisporic acids. The same protocol also provides deuterium-labeled trisporoids such as trisporin B [2H3]-19. Administration of [2H3]-19 to growing cells of the (-)-mating type of B. trispora resulted in the formation of the labeled trisporols [2H3]-20 and [2H3]-21. Growing cultures containing both mating types can be used to prepare trisporic acids from early precursors" |
| Keywords: | "Biotransformation Fatty Acids, Unsaturated/*chemical synthesis/chemistry/*metabolism Fungi/*metabolism Molecular Structure;" |
| Notes: | "MedlineSchachtschabel, Doreen Boland, Wilhelm eng Research Support, Non-U.S. Gov't 2007/01/25 J Org Chem. 2007 Feb 16; 72(4):1366-72. doi: 10.1021/jo062236c. Epub 2007 Jan 23" |
