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Synthesis, characterization, and app...

Moeller Quintavalla, Suzanne M.

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Synthesis, characterization, and applications of novel water-soluble pyridyl porphyrins.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Synthesis, characterization, and applications of novel water-soluble pyridyl porphyrins./
Author:	Moeller Quintavalla, Suzanne M.
Description:	291 p.
Notes:	Source: Dissertation Abstracts International, Volume: 65-02, Section: B, page: 0744.
Contained By:	Dissertation Abstracts International65-02B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3123445
ISBN:	0496707566

Synthesis, characterization, and applications of novel water-soluble pyridyl porphyrins.
Moeller Quintavalla, Suzanne M.

Synthesis, characterization, and applications of novel water-soluble pyridyl porphyrins. - 291 p.

Source: Dissertation Abstracts International, Volume: 65-02, Section: B, page: 0744.

Thesis (Ph.D.)--Princeton University, 2004.

The family of tetracationic N-substituted meso -pyridyl porphyrins are unique catalysts that have found use as DNA nucleases, peroxynitrite decomposition catalysts, oxidation catalysts, and photosensitizers.

ISBN: 0496707566Subjects--Topical Terms:

516206
Chemistry, Organic.

Synthesis, characterization, and applications of novel water-soluble pyridyl porphyrins.
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100 1 $a Moeller Quintavalla, Suzanne M. $3 1932447
245 1 0 $a Synthesis, characterization, and applications of novel water-soluble pyridyl porphyrins.
300 $a 291 p.
500 $a Source: Dissertation Abstracts International, Volume: 65-02, Section: B, page: 0744.
500 $a Adviser: John T. Groves.
502 $a Thesis (Ph.D.)--Princeton University, 2004.
520 $a The family of tetracationic N-substituted meso -pyridyl porphyrins are unique catalysts that have found use as DNA nucleases, peroxynitrite decomposition catalysts, oxidation catalysts, and photosensitizers.
520 $a The pyridyl porphyrins 4-PyP and 2-PyP were tetrasubstituted at the pyridyl nitrogen in good yield with a variety of alkylating agents, including iodides, tosylates, bromoesters, and bromoacetamides. The resulting free base or metallated complexes were characterized by UV spectroscopy, 1D and 2D 1H NMR, and electrospray and MALDI mass spectroscopy. Certain alkylations of meso-tetrakis(2-pyridyl)porphyrin resulted in nonstatistical distributions of atropisomers, which could be resolved by column chromatography or preparatory HPLC using a high-salt mobile phase.
520 $a Alkylation of 2-PyP with (R)-(+)-methylbenzylacetamido groups resulted in a single atropisomer, which was identified as the alphaalphabetabeta isomer by 1D and 2D 1H NMR. When treated with oxidant at pH 8.9, Mn 2-T(MBz)PyP was shown to stabilize the oxoMn(V) intermediate for 95 s. Oxidations of styrene and styrene-like substrates were performed in water using the triple salt Oxone as the oxidant. The best results were obtained for styrene oxide at 11% yield and 2.21% ee, and the best ee was obtained for cis-beta-methylstyrene at 4.4%.
520 $a A novel peroxynitrite decomposition catalyst was synthesized from 2-PyP and triethylene glycol monomethyl ether and characterized by UV, 1 H NMR, and mass spectroscopy. The iron complex of 2-T(PEG3)PyP was found to decompose peroxynitrite at a rate of 7.6 x 106 M-1 s-1 at 10 muM porphyrin. Tetraalkylated derivatives of 2-PyP were found to be inefficient DNA nucleases and bound poorly to DNA due to steric bulk above and below the porphyrin plane. In vitro and in vivo, Fe 2-T(PEG3)PyP exhibited significant cytoprotective abilities for pancreatic cells stressed with peroxynitrite and for murine models of oxidative stress-related injuries.
590 $a School code: 0181.
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Analytical. $3 586156
690 $a 0490
690 $a 0486
710 2 0 $a Princeton University. $3 645579
773 0 $t Dissertation Abstracts International $g 65-02B.
790 1 0 $a Groves, John T., $e advisor
790 $a 0181
791 $a Ph.D.
792 $a 2004
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3123445