Naturalproductman’s Blog

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Archive for the ‘Chemical Biology’ 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 »

Nuphar alkaloid chemical biology

Posted by naturalproductman on February 8, 2016

Jimmy Wu and co-workers reported in ACIE on the formal synthesis of nuphar alkaloids and their apoptotic activity. Did you know that the second “p” in “apoptosis” is silent and it is pronounced “apa-tosis”? The Greek word “apoptosis” means “falling off” or “dropping off” of flower petals or tree leaves.

 

ACIE paper

Posted in Chemical Biology, Random, Unnatural Products | Leave a Comment »

LmbF is a PLP-enzyme

Posted by naturalproductman on October 21, 2015

Jiri Janata and co-workers from ASCR in the Czech Republic have reported in Chemical Science on the identification of the enzyme, LmbF, in the biosynthesis of lincomycin.

lincomycin

Chemical Science paper

Posted in Alkaloids, Biosynthesis, Chemical Biology, Tetrahydropyrans | Leave a Comment »

Marmycin A synthesis

Posted by naturalproductman on October 13, 2015

Raphael Rodriguez and co-workers at CNRS UMR have reported in Nature Chemistry on the synthesis of marmycin A.

Nature Chemistry paper

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

Going from a diol to a tetrahydropyran in salinomycin

Posted by naturalproductman on September 25, 2015

Peter Leadlay and co-workers from the University of Cambridge have reported in ACIE on the enzyme that makes the tetrahydropyran ring in salinomycin. The tetrahydropyran is proposed to come from a diol where one of the hydroxy groups is in the beta-position to a ketone and subsequently dehydrates to form an enone. The enone undergoes an intramolecular Michael reaction to form the tetrahydropyran. However, when the reaction is done in vitro with the purified enzyme, they don’t see the enone intermediate, so I wonder if it is a processive reaction; in other words, the enone forms in the enzyme active site without being released and cyclizes to the tetrahydropyran.

salinomycin

ACIE paper

Posted in Biosynthesis, Chemical Biology, Enzymes, Mechanistic, Polyketides, Tetrahydropyran | Leave a Comment »

Asperchalasine A

Posted by naturalproductman on September 3, 2015

Here’s a natural product isolation paper that was published in ACIE. Yonghui Zhang and co-workers report on the isolation of asperchalasine A, which induced G-1 phase cell cycle arrest by reducing the expression of cyclin A, CDK2, and CDK6 in cancer cells but not in normal cells at 20 micromolar (pretty high concentration so not so potent in my opinion).

asperchalasine A

ACIE paper

Posted in Cancer, Chemical Biology, Dimer, Terpenoids | Leave a Comment »

Cyclopropenones – a chemical biology tool

Posted by naturalproductman on August 7, 2015

Jennifer Prescher and colleague at UC Irvine have reported in JACS on the potential for using cyclopropenones to conjugate proteins.

amine

JACS paper

Posted in Cascade Reactions, Chemical Biology, New Setups | Leave a Comment »

Molecular prosthetics

Posted by naturalproductman on August 7, 2015

Martin Burke’s group is making use of their small molecules that they’re synthesizing.
prosthetic
JACS paper

Posted in Chemical Biology, Macrolides, Methodology, Polyenes, Polyketides | Leave a Comment »

Nannocystin A

Posted by naturalproductman on July 17, 2015

Dominic Hoepfner and co-workers from Novartis have reported in ACIE on nannocystin A, which had similar binding properties with didemin B on EF-1alpha (elongation factor 1 inhibitor).

nannocystin A

ACIE paper

Mark Brönstrup and co-workers at Helmholtz Zentrum für Infektionsforschung also reported on the isolation of this small molecule. I wonder if there’s a relationship between the two studies.

ACIE paper

the novartis paper states that their study parallels the work in helmholtz. I guess the two studies just coincidentally resulted in the isolation of the same compound.

Posted in Biosynthesis, Cancer, Chemical Biology, Macrocycles, Macrolides, Peptides | Leave a Comment »

Staphyloferrin B synthesis

Posted by naturalproductman on July 11, 2015

Elizabeth Nolan and co-workers from MIT have reported in JACS on the synthesis of staphyloferrin B, an iron chelating natural product found in bacteria.

iron

JACS paper

Posted in Chemical Biology, Peptides, Total Synthesis | Leave a Comment »

 
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