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

US government science institute's one time police chief linked to campus meth lab

31 July 2015 News and Analysis

news image

Explosion injuring a member of the National Institute of Standards and Technology's security force uncovered methamphetamine ...

(–)-Jiadifenolide

27 July 2015 Organic Matter

news image

BRSM wonders what makes a route so good it becomes the last total synthesis of a complex target

Most Commented

Scientist imprisoned over fraudulent HIV vaccine research

6 July 2015 News and Analysis

news image

Former Iowa State University researcher gets four-and-a-half years in prison for faking vaccine research funded by the NIH

Single polymer pill could deliver entire drug course in one go

27 July 2015 Research

news image

Flexible elastomer ring springs open to stay in stomach and could slowly release drugs over days