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Archive for the ‘Enzymatic’ Category

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 »

Alcohol to carboxylic acid by an enzyme

Posted by naturalproductman on May 7, 2014

Marco Fraaije and co-workers from the University of Groningen in the Netherlands have reported in ACIE on an enzyme catalyzed oxidation of an alcohol to carboxylic acid.

aldehyde

They did a mechanistic study, which caught my attention. They wanted to test if the carboxylic acid arises from the gem-diol of the aldehyde intermediate or directly from the aldehyde. The experiment was run under 18O-labeled water with 4-nitrobenzaldehyde. They state that if the reaction is spontaneous then the aldehyde will directly give the carboxylic acid with no 18O incorporated in the product, but if it is from the gem-diol, you will have 18O-atoms.

I have a problem with this part because the reaction can still come from the aldehyde if the carboxylic acid had an 18O-atom. The way this would occur is that the aldehyde can get hydrated to the gem-diol then it would be in equilibrium with the aldehyde and give back the aldehyde but this time it has an 18O-atom (STEP 2 product of below). This aldehyde, if oxidized by the enzyme, would yield the carboxylic acid with 18O-atom.

GIF RED
Anyway, interesting paper.
ACIE paper

Posted in Enzymatic, Mechanistic, Methodology | Leave a Comment »

Selective macrocyclization

Posted by naturalproductman on April 23, 2012

Christopher Boddy and co-workers at the University of Ottawa have reported in Organic Letters on the selective macrocyclization using DEBS TE.

enzyme

OL paper

Posted in Chemical Biology, Enzymatic, Macrocycles, Macrolides, Methodology | Leave a Comment »

Diepoxide intermediate

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).

epoxidation

JACS paper

Posted in Biosynthesis, Carboxylic acids, Chemical Biology, Enzymatic, Methodology | Leave a Comment »

Heparin’s chemoenzymatic synthesis

Posted by naturalproductman on October 28, 2011

Jian Liu and co-workers at UNC have reported in Science on a chemoenzymatic synthesis of the sulfated glycan, heparin – a blood thinner.

 

Science paper

Posted in Chemical Biology, Enzymatic, Glycosides, Methodology | Leave a Comment »

Clividine synthesis

Posted by naturalproductman on July 27, 2011

Martin Banwell and co-workers at the Australian National University have reported in JOC on their synthesis of clividine.

clividine

JOC paper

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

C-C bond forming process using an enzyme

Posted by naturalproductman on July 5, 2011

Claudia Schmidt-Dannert and colleague at the University of Minnesota have reported in ACIEE on the use of BBE (berberine bridge enzyme) to selectively form a C-C bond.

enzyme

ACIEE paper

Posted in Enzymatic, Methodology, Unnatural Products | Leave a Comment »

Hydroxymethylcytosine

Posted by naturalproductman on June 19, 2011

Thomas Carrel and co-workers from Ludwig-Maximilians University in Munich have published a mini-review on hydroxymethylcytosine, a newly discovered modification of DNA – as if methylating cytosine was not enough.

DNA

ACIEE paper

Posted in Chemical Biology, Enzymatic, Proteins | Leave a Comment »

A new C35-terpene cyclase

Posted by naturalproductman on June 7, 2011

Tsutomu Sato and co-workers from Niigata University have reported in JACS on the identification of a terpene cyclase enzyme that cyclized a C35 terpene (sesquarterpene).

C35

JACS paper

Posted in Chemical Biology, Enzymatic, Methodology, Sesquarterpenes, Terpenes | Leave a Comment »

Borrelidin studies

Posted by naturalproductman on June 5, 2011

Sabine Laschat and co-workers from the Universitat Stuttgart have reported in European JOC on their studies towards borrelidin where they used CYP102A to perform a regioselective hydroxylation of an alkane.

chemoenzymatic
European JOC paper

Posted in Asymmetric, Enzymatic, Methodology | Leave a Comment »

 
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