TY - JOUR A1 - Köppen, Robert A1 - Braun, B. A1 - Wedler, C. A1 - Theil, F. T1 - Synthesis of M + 4 stable isotopomers of ergometrine and ergometrinine JF - Natural Product Communications (NPC) N2 - The priority ergot alkaloids ergometrine and ergometrinine are highly toxic mycotoxins naturally occurring in different types of grains (i.e. rye, wheat, rice), as well as grain-based foods and, therefore, have gained increasing importance for food safety over the last years. The application of HPLC-MS/MS for the analysis of ergot alkaloids in food presupposes the availability of isotopically labelled internal standards. Thus, a multistep synthesis was developed for ergometrine-(N-13CD3) and its epimer ergometrinine-(N-13CD3) with a mass shift of four units compared with the parent compounds. The synthesis is based on the preparation of stable isotope labelled lysergic acid that was coupled with (S)-alaninol. The chemical synthesis of both compounds has been achieved in six steps with an overall yield of 1 % (ergometrine-(N-13CD3)) and 0.6 % (ergometrinine-(N-13CD3)), respectively. Structural identification was performed by MS analysis as well as 1H and 13C NMR. KW - Ergometrine-(N-13CD3) KW - Ergometrinine-(N-13CD3) KW - Mycotoxin KW - Ergot alkaloids KW - Analytical standard KW - Stable isotope dilution analysis (SIDA) PY - 2017 SN - 1934-578X SN - 1555-9475 VL - 12 IS - 3 SP - 373 EP - 376 PB - NPC CY - Westerville, Ohio, USA AN - OPUS4-39874 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER -