Naturalproductman’s Blog

Hey, is that a natural product?!

Archive for the ‘Mass Spectrometry’ Category

Using carbon dating to show that tramadol is NOT a natural product afterall

Posted by naturalproductman on October 21, 2015

Remember that debate whether tramadol was really a natural product or not? Michael Spiteller and co-workers at TU Dortmund used accelerator mass spectrometry to analyze the isotopes of carbon found in tramadol found in the soil to show that tramadol is NOT a natural product. This is all based on the fact that natural organic compounds that are biosynthesized in living organisms contain amounts of 14C-radioisotope close to that of the environment.
ACIE paper

Posted in Mass Spectrometry, Unnatural Products | Leave a Comment »

Sweriledugenin A

Posted by naturalproductman on December 30, 2013

Ji-Jun Chen and co-workers at the Kunming Institute of Botany have reported in Org Lett on the isolation of sweriledugenin A.


OL paper

Posted in Anti-viral, Diseases, Lactones, Mass Spectrometry | Leave a Comment »

Asymmetric epoxidation

Posted by naturalproductman on April 19, 2013

Benjamin List and co-workers have reported in JACS on their studies of cinchona alkaloid catalyzed asymmetric epoxidation of activated olefins.


JACS paper

Posted in Asymmetric, Computational, DFT, ESI, Mass Spectrometry, Mechanistic, Methodology, Organocatalytic | Leave a Comment »


Posted by naturalproductman on December 19, 2012

At some point I’m going to need to review principal component analysis to truly understand this metabolomics study that identified a small molecule phermone.

ACIE paper

Posted in Computational, Mass Spectrometry, Metabolomics | Leave a Comment »

Determination of stereochemistry on a small scale

Posted by naturalproductman on December 5, 2012

Scptt Rychnovsky and co-workers have reported in JACS on a clever way to determine the stereochemical configuration of a primary amine by using mass spectrometry.  This may be useful when you only have a small amount of material.


JACS paper

Posted in Asymmetric, Kinetic resolution, Mass Spectrometry, Methodology | Leave a Comment »

Named reaction refresher

Posted by naturalproductman on January 19, 2012

The Criegee rearrangement converts a tertiary alcohol into an alcohol and a ketone by using a peroxy acid and in turn forming peroxide intermediate that breaks down and forms the products.  In an ozonolysis, after the [3+2] between an ozone molecule and an alkene, the five membered ring breaks down to  a carbonyl and a carbonyl dioxide intermediate, which is called a “Criegee inermediate”.

Craig Taatjes and co-workers from Sandia National Laboratories have reported in Science on the observation of the Criegee intermediate by mass spec in the gas phase by reacting a methyl iodide radical and oxygen.


Science paper

Posted in Criegee rearrangement, Mass Spectrometry, Mechanistic, Methodology, Named Reactions | Leave a Comment »

TS analog complexed with protein and water

Posted by naturalproductman on January 17, 2012

Vern Schramm and co-workers at Albert Einstein College of Medicine have reported in JACS on the observation of a complex between a transition state analog and an enzyme, methylthioadenosine/S-adenosylhomocysteine nucleosidase through mass spectrometry.

transition state

JACS paper

Posted in Chemical Biology, Enzymes, Mass Spectrometry, Mechanistic, Proteins | Leave a Comment »

Evidence of iron-oxo

Posted by naturalproductman on October 13, 2011

Miquel Costas and co-workers at Universitat de Girona in Spain have reported in Nature Chemistry on the observation of an iron-oxo complex using mass spectrometry.

mass spec

Nature Chemistry paper

Posted in Computational, DFT, Iron, Mass Spectrometry, Mechanistic, Methodology, Transition Metal | Leave a Comment »