From algae to crystalline sponge

Although not as exciting as it used to be, Fujita’s crystalline sponge technology has reached another milestone. This time the group could determine the absolute configuration of a natural product elatenyneBurton lab from Oxford attempted (and not once) the total synthesis of the product with a sole purpose to assign its structure and absolute configuration. But to achieve that, one needs a good reference analytical data of the natural sample in the first place. And this was the bottleneck for the featured compound. Owing to its almost symmetrical structure, the molecule doesn’t rotate the polarized light by a lot (the latest [α]D values from Burton and Kim labs were −1.6° and +0.80° for two enantiomers). But reported data for ‘natural’ elatenyne varied from +19° to −10°. Which would make ambiguous even a qualitative judgement about the synthesized compound.

elatenyne.png
Structure of elatenyne is almost σ-symmetric

And as you can imagine, the molecule doesn’t easily crystallize in a conventional way. So it was an ideal case to try soaking a crystalline sponge in a solution of the compound. Remarkably, Fujita’s group needed only 5 μg of the freshly isolated compound for the analysis. As the result, they confirmed that Burton’s structure was correct.

No comments on bioactivity though.

Author: Slava Bernat

I did my PhD in medicinal chemistry/chemical biology of G protein-coupled receptors and then explored some chemical biology of non-coding RNA as a postdoc. Currently I'm working in a small biotech company in San-Francisco Bay area as a research chemist. I'm writing about science, which catches my attention in rss feed reader and some random thoughts or tutorials.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

breakingthemarket.com/

profiting from randomness

R-statistics blog

Statistics with R, and open source stuff (software, data, community)

Colorblind Chemistry

The blog of Marshall Brennan, PhD

ACS Careers Blog

Career advice from the American Chemical Society

Lab Without Benches

Career skills for scientists

amphoteros

forcing molecules to behave

Chemjobber

mostly science

Org Prep Daily

synthetic procedures I tried and liked

Sussex Drug Discovery Centre

Medicinal, Chemistry and Biochemistry blog from the Sussex Drug Discovery Centre

Practical Fragments

mostly science

Chemical connections

...chemistry & other curiosities

Just Like Cooking

mostly science

%d bloggers like this: