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A facile synthesis of 3,3,4,4,3′,3′,4′,4′‐homocystine‐ d 8
Author(s) -
Adamczyk Maciej,
Fishpaugh Jeffrey R.,
Thiruvazhi Mohan
Publication year - 2000
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 - 10.1002/1099-1344(200008)43:9<909::aid-jlcr376>3.0.co;2-9
Subject(s) - chemistry , chemical synthesis , methanol , high performance liquid chromatography , derivative (finance) , homocysteine , mass spectrometry , sulfide , glycine , chromatography , medicinal chemistry , organic chemistry , biochemistry , in vitro , amino acid , economics , financial economics
We describe the synthesis of 3,3,4,4,3′,3′,4′,4′‐homocystine‐ d 8 2 in four steps. Compound 2 has been utilized as an internal standard for the LC‐MS quantification of L‐homocysteine 1 , a marker for cardiac disease. 1,1,2,2‐Tetradeutero‐2‐bromoethyl triphenylmethyl sulfide 4 was treated with the dianion of N ‐( tert ‐butoxycarbonyl) glycine tert ‐butyl ester 5 giving the homocysteine derivative 6 . Oxidation of 6 with iodine in methanol gave the homocystine precursor 7 . Subsequent deprotection provided 2 in high chemical purity (99%) as measured by analytical HPLC and isotopic purity of >99% as determined by mass spectrometry. Copyright © 2000 John Wiley & Sons, Ltd.