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Nitrous‐Acid‐Mediated Synthesis of Iron–Nitrosyl–Porphyrin: pH‐Dependent Release of Nitric Oxide
Author(s) -
Bhuyan Jagannath,
Sarkar Sabyasachi
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201200518
Subject(s) - chemistry , ferrous , porphyrin , triphenylphosphine oxide , nitric acid , nitric oxide , inorganic chemistry , nitrous oxide , nitrous acid , oxygen , photochemistry , medicinal chemistry , triphenylphosphine , organic chemistry , catalysis
Abstract Two iron–nitrosyl–porphyrins, nitrosyl[ meso ‐tetrakis(3,4,5‐trimethoxyphenylporphyrin]iron(II) acetic acid solvate ( 3 ) and nitrosyl[ meso ‐tetrakis(4‐methoxyphenylporphyrin]iron(II) CH 2 Cl 2 solvate ( 4 ), were synthesized in quantitative yield by using a modified procedure with nitrous acid, followed by oxygen‐atom abstraction by triphenylphosphine under an argon atmosphere. These nitrosyl porphyrins are in the {FeNO} 7 class. Under an argon atmosphere, these compounds are relatively stable over a broad range of pH values (4–8) but, under aerobic conditions, they release nitric oxide faster at high pH values than that at low pH values. The generated nitric‐oxide‐free iron(III)–porphyrin can be re‐nitrosylated by using nitrous acid and triphenylphosphine. The rapid release of NO from these Fe II complexes at high pH values seems to be similar to that in nitrophorin, a nitric‐oxide‐transport protein, which formally possesses Fe III . However, because the release of NO occurs from ferrous–nitrosyl–porphyrin under aerobic conditions, these compounds are more closely related to nitrobindin, a recently discovered heme protein.