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Synthesis of a ‘twisted’ transition-state analogue of biotin |
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| Authors: | Andrew S Grant Kleem Chaudhary Andrea Peters Andreas Decken |
| Institution: | a Department of Chemistry, Mount Allison University, Sackville, NB, Canada E4L 1G8 b Department of Chemistry, University of Winnipeg, Winnipeg, MB, Canada R3B 2E9 c Department of Chemistry, University of New Brunswick, Fredericton, NB, Canada E3B 6E2 |
| Abstract: | A facile, racemic synthesis of a ‘twisted’ transition-state analogue of biotin is described. A key reaction is the electronically assisted ring-closure of the sulfur containing ring by displacement of an in situ generated mesylate by a suitably positioned 4-methoxybenzyl sulfide. The crystal structure of tricyclic compound 6 shows the AB ring system to indeed be twisted. The ‘twist’ was introduced to examine the possible involvement of sulfur participation in biotin biochemistry. |
| Keywords: | Organic synthesis Bioorganic |
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