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Archive for the ‘Enzymatic’ Category

Patent review – biocatalysts

Posted by naturalproductman on April 8, 2016

David Hughes at Cidara Therapeutics reported in ORPD on a patent literature search pertaining the use of biocatalysts to effect chemical transformations. He covers some P450 mediated cyclopropanation, reductive amination, Diels-Alder (artificial enzyme), nitrilase (conversion of nitrile to carboxylic acid)  reactions all catalyzed by enzymes.


ORPD paper

Posted in Biocatalysis, Chemical Biology, Chemoenzymatic, Enzymatic | Leave a Comment »

Biosynthetic origin of L-allo-isoleucine in desotamides and marformycins

Posted by naturalproductman on January 18, 2016

Jianhua Ju and co-workers at the Chinese Academy of Sciences have reported in JACS on the biosynthetic origin of L-allo-isoleucine. The culprit is a PLP-enzyme.


JACS paper

Posted in Biosynthesis, Enzymatic, Enzymes, Peptides | 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.


ACIE paper

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

Combining chemical and enzymatic synthesis

Posted by naturalproductman on November 29, 2014

Kevin Reynolds and co-workers from Portland State University have reported in JOC on the synthesis of premarineosin analogs using a chemo-enzymatic approach.


JOC paper

Posted in Alkaloids, Chemical Biology, Enzymatic, Methodology, Total Synthesis, Unnatural Products | 1 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.


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.


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.

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.


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).


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.


JOC paper

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