Related Experiment Video

Updated: Jul 23, 2026

Mass Spectrometric Analysis of Glycosphingolipid Antigens
13:09

Mass Spectrometric Analysis of Glycosphingolipid Antigens

Published on: April 16, 2013

Migrastatin and dorrigocins are shunt metabolites of iso-migrastatin

Jianhua Ju1, Si-Kyu Lim, Hui Jiang

  • 1Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin-Madison, Madison, WI 53705, USA.

Journal of the American Chemical Society
|February 11, 2005
PubMed

Insights

Streptomyces platensis produces iso-migrastatin (4), which converts to other compounds (1-3, 5). This study identifies iso-migrastatin as the sole natural product, with others being shunt metabolites formed via a water-mediated rearrangement.

Area of Science:

  • Microbiology
  • Natural Product Chemistry
  • Biochemistry

Background:

  • Streptomyces platensis NRRL18993 typically produces migrastatin, dorrigocin A, dorrigocin B, and 13-epi-dorrigocin A.
  • Supplementation with XAD-16 resin alters the fermentation outcome, leading to exclusive production of iso-migrastatin.

Purpose of the Study:

  • To identify the true natural product biosynthesized by S. platensis.
  • To elucidate the relationship between iso-migrastatin and other related compounds.
  • To determine the mechanism of interconversion between these compounds.

Main Methods:

  • Fermentation of Streptomyces platensis with and without XAD-16 resin.
  • In vitro stability studies in aqueous solutions.
  • Stereochemical analysis of the compounds.
  • Isotope labeling studies using H218O to investigate the rearrangement mechanism.

Main Results:

  • Fermentation with XAD-16 resin exclusively produced iso-migrastatin (4).
  • Compounds 1, 2, 3, and 5 were stable in aqueous solution, while 4 rapidly converted to them.
  • Iso-migrastatin (4) was identified as the sole bona fide natural product, with 1, 2, 3, and 5 identified as its shunt metabolites.
  • The stereochemistry of compounds 2-5 was established, except for C-11 in 3 and 4.
  • A mechanism for the H2O-mediated regio- and stereospecific rearrangement of 4 to 1, 2, 3, and 5 was proposed and supported by 18O incorporation.

Conclusions:

  • Iso-migrastatin (4) is the primary natural product synthesized by S. platensis.
  • The other identified compounds (1, 2, 3, 5) are derived from iso-migrastatin through a water-mediated rearrangement process.
  • This study clarifies the biosynthetic pathway and interconversion of these important microbial metabolites.

More Related Videos

Fatty Acid 13C Isotopologue Profiling Provides Insight into Trophic Carbon Transfer and Lipid Metabolism of Invertebrate Consumers11:14

Fatty Acid 13C Isotopologue Profiling Provides Insight into Trophic Carbon Transfer and Lipid Metabolism of Invertebrate Consumers

Published on: April 17, 2018

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Related Concept Videos

Stereoisomerism02:52

Stereoisomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
Golgi Matrix Proteins01:12

Golgi Matrix Proteins

Golgi matrix proteins are a group of highly dynamic proteins that maintain the stacked structure of Golgi. These proteins adapt to rapid morphological changes of the Golgi during the cell cycle. During cell division, mild proteolysis removes these connections resulting in Golgi unstacking. In The daughter cells, these proteins help reassemble the unstacked Golgi.
One of the first identified Golgi matrix proteins was GM130, a rod-like protein located in the cis-Golgi. Subsequently, many Golgi...
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...
Multi-pass Transmembrane Proteins and β-barrels01:09

Multi-pass Transmembrane Proteins and β-barrels

In multi-pass transmembrane proteins, the polypeptide chain crosses the membrane more than once. The transmembrane polypeptide chain either forms an α-helix or β-strand structure. α-Helix containing multi-pass transmembrane proteins are ubiquitous, whereas β-strand containing ones are mainly found in gram-negative bacteria, mitochondria, and chloroplasts.
α-Helix containing multi-pass transmembrane proteins
Multi-pass transmembrane proteins such as G-protein-linked receptors (GPCRs) and...
Gas Chromatography–Mass Spectrometry (GC–MS)01:14

Gas Chromatography–Mass Spectrometry (GC–MS)

Gas chromatography–mass spectrometry (GC–MS) is the combination of analytical techniques of gas chromatography and mass spectrometry in a single instrument for analyzing a mixture of compounds. The gas chromatograph separates the compounds in the mixture, and the mass spectrometer analyzes each compound separately to determine the molecular masses and molecular structures.
A gas chromatograph consists of a long, narrow capillary column with a polysiloxane coating on the inner wall. The coating...
Probiotics01:22

Probiotics

Probiotics are live, non-pathogenic microorganisms that confer health benefits by modulating the gut microbiota. The human gastrointestinal tract harbors a complex microbial ecosystem, and the balance of this microbiota is crucial for digestive and systemic health. Among the most extensively studied and utilized probiotics are species formerly classified within the genera Lactobacillus and Bifidobacterium. These organisms not only naturally colonize the human gut but are also consumed through...