Michael Muller and co-workers reported in JACS on the identification of some P450 enzymes involved in dimerizing polyketide natural products.
Archive for the ‘Biosynthesis’ Category
Posted by naturalproductman on April 18, 2014
Posted by naturalproductman on March 17, 2014
Someone has brought to my attention the isolation of a recent alkaloid containing a strange alkynol attached to a nitrogen.
The main supporting evidence for this structure is the 3-bond HMBC correlation of the OH proton to the alkyne carbon taken in DMSO (the alcohol is at ~9.8 ppm). The fishy thing here is that there is no 2-bond HMBC correlation (I assume it would be two bond from O-H and C-O) from the OH to the nearest alkyne carbon.
An interesting question would be how this alkynol would be introduced in the biological system. Alkynes are usually precursors to alkynols in P450 reactions and give rise to a rearrangement to form ketenes, which inactivate the enzymes.
Synthetically, I first saw alkynol structures from Sergey Kozmin’s work back in 2006. I should say that even here they are not alkynols – they are siloxy alkynes.
Perhaps anybody else has an opinion on this interesting structure?
Posted by naturalproductman on September 5, 2013
Michelle Chang and co-workers at Berkeley have reported in Science on a way to access fluorinated natural products using fluoroacetate as the building block.
Posted by naturalproductman on August 3, 2013
Ikuro Abe and co-workers from the University of Tokyo have reported in Tetrahedron on how they reconstituted the biosynthetic pathway for andrastin A in a fungus.
Posted by naturalproductman on November 21, 2012
Looking at this molecule, one would never think that you can mix three things, a penta-substituted benzene ring, benzaldehyde and humulene, and obtain the final compound, guajadial! Ji-Kai Liu and co-workers at the Kunming Institute of Botany did such a thing!
Posted by naturalproductman on October 30, 2012
Jurgen Rohr and co-workers from the University of Kentucky have reported in JACS on a Baeyer-Villiger reaction in the glivocarcin and jadomycin biosynthesis.
Posted by naturalproductman on April 20, 2012
Hideaki Oikawa and co-workers at Hokkaido University have reported in JACS on a sequential epoxidation of a bis olefin compound to yield a diepoxide that undergoes a ring opening cascade to form two cyclic polyethers (a tetrahydropyran and tetrahydrofuran).
Posted by naturalproductman on March 30, 2012
Tadeusz Molinski and co-workers have reported in JNP on the biosynthesis study of benzoscpetrin C and nagelamide H.
Posted by naturalproductman on December 2, 2011
Andreas Kirschning and co-workers at have reported in ACIEE on a combined biosynthesis/chemical synthesis approach to synthesize new ansamitocin analogs.
Posted by naturalproductman on November 19, 2011
Vahe Bandarian and colleague at the University of Arizona have reported in Biochemistry on the biosynthetic study of demethylwyosine.