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Preparation of trans‐octaethylchlorin‐D 2 (α,β),‐D 2 (γ,δ), and ‐d 4 as well as octaethylporphyrin‐d 2 using acid‐catalyzed exchange reaction
Author(s) -
Salehi Asaad,
Fonda Harold N.,
Oertling Anthony W.,
Babcock Gerald T.,
Chang Chi K.
Publication year - 1988
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.2580251207
Subject(s) - chemistry , deuterium , dehydrogenation , catalysis , hydrogen–deuterium exchange , hydrogen , proton , medicinal chemistry , organic chemistry , quantum mechanics , physics
Preparation of three forms of selectively deuterated trans‐octaethylchlorin (t‐OEC) and octaethylporphyrin‐d 2 (OEP‐d 2 ) with high isotopic purity using acid catalyzed hydrogen‐deuterium exchange reaction is described. Deuterated t‐OEC labeled at γ,δ‐methine carbons was prepared directly by equilibrating t‐OEC in D 2 SO 4 :D 2 O (6:1, v/v) at room temperature for 20 hours. t‐OEC labeled at all four methine carbons was prepared as above in 72 hours. And t‐OEC labeled at α,β‐positions was obtained by “back‐exchange” of t‐OEC‐d 4 under the protio condition, H 2 SO 4 :H 2 O (6:1, v/v), in 18 hours. The DDQ dehydrogenation of either dideuterochlorin species resulted in the formation of OEP‐d 2 . The isotopic purities of all deuterated compounds were over 98 percent except for t‐OEC‐d 2 (α,β) which was estimated to be ∼ 90 percent by proton NMR spectroscopy.