127136-20-3Relevant academic research and scientific papers
Synthesis of indoles and L-tryptophans specifically 2H- or 13C-labelled in the six-membered ring
Berg, Ellen M. M. van den,Liemt, Willem B. S. van,Heemskerk, Bram,Lugtenburg, Johan
, p. 304 - 313 (2007/10/02)
(4-2H)-, (5-2H)-, (6-2H)-, (7-2H)-, (4-13C)- and (5-13C)-1H-indole and the corresponding six L-tryptophans have been synthesized from simple labelled starting materials via a single reaction scheme.The L-tryptophans were prepared from the indoles via a quantitative one-step biosynthetic conversion.A scheme leading to the synthesis of three other indoles, mono-13C-enriched in the six-membered ring, has been developed and optimized.Indole and L-tryptophan, 13C- or 2H-enriched at the positions 4 or 5, have been synthesized with 99percent isotope incorporation without scrambling. (6-2H)-1H-Indole and -tryptophan have been synthesized with 95percent deuterium incorporation and (7-2H)-1H-indole and -tryptophan with 96percent.The reactions have been carried out on a gram scale and, in the case of the 4-13C system, they have been scaled up to the ten-gram level with no deterioration in yield.
