Synthesis of long-chain fatty acid enol esters isolated from an environmental DNA clone.
[structure: see text] Long-chain fatty acid enol ester 1 is the major metabolite of a new family of small molecules isolated from the heterologous expression of environmentally derived DNA. A versatile synthesis of 1, in which an aromatic acetaldehyde is O-acylated with a long-chain acyl chloride allowed for the rapid construction of both the isolated product (1) and a number of structural analogues (including 8, 17, and 18).
Brady
Sean F
SF
Department of Chemistry and Chemical Biology, Cornell University, Baker Laboratory, Ithaca, New York 14853-1301, USA.
Clardy
Jon
J
D000213:Acyl Carrier Protein / Q000235:genetics; D019730:Carbon-Sulfur Ligases / Q000235:genetics; D003001:Cloning, Molecular; D004269:DNA, Bacterial / Q000235:genetics*; D005227:Fatty Acids / Q000138:chemical synthesis*; D005810:Multigene Family; D014176:Protein Biosynthesis; D012988:Soil Microbiology
D000213:Acyl Carrier Protein; D004269:DNA, Bacterial; D005227:Fatty Acids; D019730:Carbon-Sulfur Ligases; C018749:long-chain-fatty-acid-(acyl-carrier-protein) ligase