Naturalproductman’s Blog

Hey, is that a natural product?!

Archive for the ‘Biosynthesis’ Category

Penitrem biosynthesis

Posted by naturalproductman on April 12, 2015

Hideaki Oikawa and co-workers at Hokkaido University have reported in ACIE on the enzymatic biosynthesis of penitrem.

alkaloid

ACIE paper

Posted in Biosynthesis, Cyclobutanes, Diterpene, Enzymes, Indoles | Leave a Comment »

Corvol ethers A and B biosynthesis

Posted by naturalproductman on March 25, 2015

Jeroen Dickschat and co-workers at Technische Universität Braunschweig have reported in ACIE on some terpene biosynthesis by characterizing a sesquiterpene cyclase enzyme.

terpene
ACIE paper

Posted in Biosynthesis, Enzymes, Sesquiterpenes | Leave a Comment »

Terpene cyclization involving carbons switching

Posted by naturalproductman on March 5, 2015

Tomohisa Kuzuyama and co-workers at the University of Tokyo have reported in ACIE on an mechanistically interesting terpene cyclization involving two carbons switching.

terpene

ACIE paper

Posted in Biosynthesis, Enzymes, Mechanistic, Proteins | Leave a Comment »

Cycloclavine biosynthesis

Posted by naturalproductman on March 5, 2015

Sarah O’Connor and co-workers from the John Innes Centre in the UK have reported in ACIE on the biosynthesis of cycloclavine.

cycloclavine

ACIE paper

Posted in Alkaloids, Biosynthesis, Enzymatic, Enzymes, Methodology | Leave a Comment »

Tetracycline analogs

Posted by naturalproductman on February 22, 2015

Hrvoje Petkovic and co-workers at University of Ljubljana have reported in ACIE on a biosynthetic engineering approach to produce new tetracycline compounds.

tetracycline

ACIE paper

Posted in Biosynthesis, Chemical Biology, Polyketides, Tetracycline | Leave a Comment »

Anditomin biosynthesis

Posted by naturalproductman on October 4, 2014

Ikuro Abe and co-workers from the University of Tokyo have reported in JACS on a biosynthetic study of anditomin.

biosynthesis

JACS paper

Posted in Biosynthesis, Meroterpenoids | Leave a Comment »

Merochlorins A and B syntheses, enzymatically

Posted by naturalproductman on August 18, 2014

Bradley Moore and Phil Baran’s groups teamed up to synthesize merochlorin A and B.

Merochlorin

ACIE paper

Posted in Biosynthesis, Chemical Biology, Enzymatic, Polyketides, Total Synthesis | Leave a Comment »

Polyketide dimerizing P450s

Posted by naturalproductman on April 18, 2014

Michael Muller and co-workers reported in JACS on the identification of some P450 enzymes involved in dimerizing polyketide natural products.

JACS paper

Posted in Biosynthesis, Polyketides | Leave a Comment »

Fumigatoside A

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?
alkynol

OL paper

Posted in Alkaloids, Biosynthesis | 2 Comments »

Fluorinated compounds, biosynthetically

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.

 

Science paper

Posted in Biosynthesis, Unnatural Products | Leave a Comment »

 
Follow

Get every new post delivered to your Inbox.

Join 78 other followers