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Title: Synthesis and characterization of models for heme-containing proteins

Abstract

The synthesis of a series of blocked and imidazole appended diphenylporphyrins is described. The hybrid porphyrin is synthesized by the condensation of o-nitrobenzaldehyde with 4,4'-diethyl-3,3'-dimethyl-2,2'-dipyrrylmethane in methanol followed by oxidation and reduction. The effectiveness of the blocking groups is supported by the formation of stable ferric hydroxides in the doubly protected system; trans 5, 15-bis(o-(p-t-butylbenzamido)phenyl)-2,8,12,18-tetraethyl-3,7,13,17-tetramethylporphyl. This complex was characterized by UV-visible, /sup 1/H NMR, IR and cyclic voltammetry. The ability of the m-benzamido linkage to enforce imidazole coordination is shown by /sup 1/H NMR studies on the ferric bis imidazole complexes of free, and covalently linked systems. Synthetic analogues of hydroporphyrins are constructed from gemini-alkylated ketones resulting from the oxidation of octaethyl porphyrin. The synthesis of simple chlorins, bacteriochlorins, isobacteriochlorins, and imidazole linked systems are described. These stabilized hydroporphyrins are fully characterized by UV-visible, /sup 1/H NMR, and cyclic voltammetry.

Authors:
Publication Date:
Research Org.:
Michigan State Univ., East Lansing (USA)
OSTI Identifier:
6551031
Resource Type:
Thesis/Dissertation
Resource Relation:
Other Information: Thesis (Ph. D)
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; PORPHYRINS; CHEMICAL COMPOSITION; CHEMICAL PREPARATION; HEME; MATHEMATICAL MODELS; NMR SPECTRA; NUCLEAR MAGNETIC RESONANCE; PROTONS; REDOX REACTIONS; VOLTAMETRY; BARYONS; CARBOXYLIC ACIDS; CHEMICAL REACTIONS; ELEMENTARY PARTICLES; FERMIONS; HADRONS; HETEROCYCLIC ACIDS; HETEROCYCLIC COMPOUNDS; MAGNETIC RESONANCE; NUCLEONS; ORGANIC ACIDS; ORGANIC COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; PIGMENTS; RESONANCE; SPECTRA; SYNTHESIS; 550200* - Biochemistry

Citation Formats

Young, R H. Synthesis and characterization of models for heme-containing proteins. United States: N. p., 1986. Web.
Young, R H. Synthesis and characterization of models for heme-containing proteins. United States.
Young, R H. Wed . "Synthesis and characterization of models for heme-containing proteins". United States.
@article{osti_6551031,
title = {Synthesis and characterization of models for heme-containing proteins},
author = {Young, R H},
abstractNote = {The synthesis of a series of blocked and imidazole appended diphenylporphyrins is described. The hybrid porphyrin is synthesized by the condensation of o-nitrobenzaldehyde with 4,4'-diethyl-3,3'-dimethyl-2,2'-dipyrrylmethane in methanol followed by oxidation and reduction. The effectiveness of the blocking groups is supported by the formation of stable ferric hydroxides in the doubly protected system; trans 5, 15-bis(o-(p-t-butylbenzamido)phenyl)-2,8,12,18-tetraethyl-3,7,13,17-tetramethylporphyl. This complex was characterized by UV-visible, /sup 1/H NMR, IR and cyclic voltammetry. The ability of the m-benzamido linkage to enforce imidazole coordination is shown by /sup 1/H NMR studies on the ferric bis imidazole complexes of free, and covalently linked systems. Synthetic analogues of hydroporphyrins are constructed from gemini-alkylated ketones resulting from the oxidation of octaethyl porphyrin. The synthesis of simple chlorins, bacteriochlorins, isobacteriochlorins, and imidazole linked systems are described. These stabilized hydroporphyrins are fully characterized by UV-visible, /sup 1/H NMR, and cyclic voltammetry.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1986},
month = {1}
}

Thesis/Dissertation:
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