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Facile Access to Isotopically Labelled Valylleucyl Anilides as Biomarkers for the Quantification of Hemoglobin Adducts to Toxic Electrophiles
Author(s) -
Belov Vladimir N.,
Müller Michael,
Ignatenko Oleg,
Hallier Ernst,
de Meijere Armin
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500429
Subject(s) - chemistry , derivatization , electrophile , hydrogenolysis , adduct , acrylonitrile , hemoglobin , epichlorohydrin , organic chemistry , chromatography , high performance liquid chromatography , catalysis , polymer , copolymer
An easy and efficient synthesis of valylleucyl anilide (HValLeuNHPh) and labelled HVal( 13 C 5 , 15 N)LeuNHPh has been developed. Derivatization of these substances with oxirane, acrylonitrile, epichlorohydrin, glyceraldehyde and other aldehydes gives a series of reference substances and internal standards for the quantitative evaluation of human exposure to toxic electrophiles by quantitative determination of their hemoglobin adducts. Coupling of N ‐Z‐ N ‐Me‐Val( 13 C 5 , 15 N)OH with HLeuNHPh followed by hydrogenolysis affords N –Me–Val( 13 C 5 , 15 N)LeuNHPh for quantification of the exposure to methylating agents. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)