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Synthesis of deuterium‐labeled (24 R )‐methyl brassinosteroids
Author(s) -
Khripach Vladimir A.,
Zhabinskii Vladimir N.,
Gulyakevich Olga V.,
Ermolovich Yurii V.,
Konstantinova Olga V.
Publication year - 2011
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.1874
Subject(s) - chemistry , deuterium , lithium (medication) , methyl group , side chain , transformation (genetics) , tritium , stereochemistry , brassinosteroid , isotopic labeling , organic chemistry , alkyl , biochemistry , medicine , physics , quantum mechanics , arabidopsis , nuclear physics , mutant , gene , endocrinology , polymer
Synthesis of labeled brassinosteroids (24‐epibrassinolide and its biosynthetic precursors) containing three deuterium atoms in the terminal part of the side chain is reported. Labeling was achieved by three‐step reductive transformation of carbethoxy group into methyl using lithium aluminium deuteride. The proposed method ensured high isotopic purity of (24 R )‐methyl brassinosteroids containing a label in a position which is not subjected to its loss. Copyright © 2011 John Wiley & Sons, Ltd.