I recently analysed NMR data for one of my pure compounds and there was a singlet peak (1H NMR) integrating for 18H. My supervisor has said that no natural product comes with a t-butyl moiety and my compound may be a contaminant or plasticizer. Is it because having two t-butyl groups would be bulky and is biosynthetically not probable?
Mr. Sinclair,
Has your supervisor knowledge about the structure of all natural products in the nature?
18H would require two equivalent t-butyl groups. That I would call unlikely.
Dear James
Although natural products containing tert-butyl groups are considered to be rare, several different substance classes such as peptides, terpenes, carbinols, esters and even a ketone bearing a tert-butyl group have been described in the literature.
Check this two links, they could be usefull to you.
https://doi.org/10.1016/S0040-4020(01)80873-5
http://pubs.rsc.org/en/content/articlelanding/2008/ob/b800083b/unauth#!divAbstract
Another example, confirmed by total synthesis. PM060184 is in phase II clinical trials http://pubs.acs.org/doi/abs/10.1021/ja404578u
Apparently 2,4-di-tert-butylphenol is produced by dozens of different organisms. I am still in two minds as to whether this is true, or the result of either environmental contamination or bad lab technique. The more I read on this topic the more it seems it is indeed a natural product. It could be easily resolved by conducting an experiment where 13C-glucose is used as the sole carbon source...
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