677347-87-4Relevant academic research and scientific papers
Synthesis of a 'twisted' transition-state analogue of biotin
Grant, Andrew S.,Chaudhary, Kleem,Stewart, Lisa,Peters, Andrea,Delisle, Spencer,Decken, Andreas
, p. 1777 - 1780 (2004)
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.
