Coral animal chemical structures solved


breitfussin

Structure of breitfussin A © Wiley-VCH

A combination of atomic force microscopy (AFM) and computational techniques have been used to solve the unusual structures of two natural products from the Arctic coral-like animal, Thuiaria breitfussi. The compounds, known as breitfussins, have been difficult to study as they are only available in small amounts, preventing analysis by x-ray crystallography. Previously, researchers have used the standard techniques of mass spectrometry and NMR to identify indole, oxazole and pyrrole aromatic groups but could not piece them together.

By imaging the breitfussin molecules using AFM, the connections between the groups were clear and revealed that their unusual structures could be derived from the dipeptide proline–tryptophan. This technique was employed by the same team from IBM who previously rose to fame with their 2009 paper in Science where they were able to image molecules with individual atoms resolved. However, AFM was unable to differentiate between the oxygen and nitrogen in the oxazole ring and so the researchers could not place them confidently. Using computational approaches, the researchers calculated the expected 1H and 13C NMR chemical shifts and compared them to the experimental values to determine their positions.


Related Content

Life in the freeze frame

26 August 2014 Premium contentFeature

news image

Using x-rays to probe biological molecules has revolutionised science. Clare Sansom looks at a century of progress

Crystal clear

13 December 2013 Premium contentFeature

news image

With the international year of crystallography upon us, Clare Sansom celebrates this important discipline

Most Read

Self-cleaning sensors see the light

23 January 2015 Research

news image

Overcoming electrode fouling in biomedical and environmental detectors

Alkali metal explosion explained

26 January 2015 Research

news image

High-speed cameras help re-examine the chemistry behind a classic classroom demonstration

Most Commented

Alkali metal explosion explained

26 January 2015 Research

news image

High-speed cameras help re-examine the chemistry behind a classic classroom demonstration

What we mean when we talk about bonds

29 January 2015 Comments

news image

Santiago Alvarez delves into the debates and disagreements that surround one of chemistry's most fundamental concepts