Title: Oxidative Degradation of Zinc Porphyrin in Comparison with Its Iron Analogue
Abstract: Chemistry – A European JournalVolume 16, Issue 35 p. 10649-10652 Communication Oxidative Degradation of Zinc Porphyrin in Comparison with Its Iron Analogue Jagannath Bhuyan, Jagannath Bhuyan Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur-208016, U.P. (India), Fax: (+91) 512-259-7265Search for more papers by this authorProf. Sabyasachi Sarkar, Prof. Sabyasachi Sarkar [email protected] Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur-208016, U.P. (India), Fax: (+91) 512-259-7265Search for more papers by this author Jagannath Bhuyan, Jagannath Bhuyan Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur-208016, U.P. (India), Fax: (+91) 512-259-7265Search for more papers by this authorProf. Sabyasachi Sarkar, Prof. Sabyasachi Sarkar [email protected] Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur-208016, U.P. (India), Fax: (+91) 512-259-7265Search for more papers by this author First published: 04 August 2010 https://doi.org/10.1002/chem.201001073Citations: 28Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Graphical Abstract Solar conversion: Zinc hydroxyisoporphyrin (2), under sunlight and argon, is reduced back to zinc meso-tetraphenylporphyrin (1), but stays stable in oxygen in the absence of light. This behavior is in contrast to its iron analogue and stresses the redox role of iron in heme degradation. Compound 2 also responds to chlorophyll-type degradation (3) under sunlight and oxygen. References 1 1aK. M. Barkigia, M. G. Renner, H. Xie, K. M. Smith, J. Fajer, J. Am. Chem. Soc. 1993, 115, 7894– 7895; 1bH. Segawa, R. Azumi, T. Shimidzu, J. Am. Chem. Soc. 1992, 114, 7564– 7565; 1cJ. L. Sessler, R. S. Zimmerman, C. Bucher, V. Kral, B. Andrioletti, Pure Appl. Chem. 2001, 73, 1041– 1057; 1dJ. P. Evans, F. Niemevz, G. Buldain, P. O. Montellano, J. Biol. Chem. 2008, 283, 19530– 19539. 2 2aH. Xie, K. M. Smith, Tetrahedron Lett. 1992, 33, 1197– 1200; 2bY. Takeda, S. Takahara, Y. Kobayashi, H. Misawa, H. Sakuragi, K. Tokumaru, Chem. Lett. 1990, 2103– 2106; 2cA. Gold, W. Ivey, G. E. Toney, R. Sangaiah, Inorg. Chem. 1984, 23, 2932– 2935. 3 3aR. B. Woodward, Angew. Chem. 1960, 72, 651– 662; 3bR. B. Woodward, Pure Appl. Chem. 1961, 2, 383– 404; 3cR. B. Woodward, Bull. Fed. Ind. Chim. Belg. 1962, 27, 1293– 1308. 4D. Dolphin, R. H. Felton, D. C. Borg, J. Fajer, J. Am. Chem. 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Crystallographic data for 2: C44H31N5O5Zn, Mr=775.09, 0.20×0.10×0.08 mm3, monoclinic, a=12.910(5) Å, b=11.244(5) Å, c=24.241(5) Å, α=90.005(5)°, β=92.287(5)°, γ=90.005(5)°, V=3516.0(2) Å3, space group P21/c, Z=4 R1=0.0603 λ(MoKα)=0.71073 Å, T=100(2) K, 22 805 reflections, 8660 unique, Rint=0.0838, R1=0.060, wR2=0.137. 10K. Rachlewicz, L. Latos-Grazynski, Inorg. Chem. 1995, 34, 718– 727. 11D. Bhattacharya, S. Sarkar, Eur. J. Inorg. Chem. 2010, 3429– 3435. 12DFT calculations have been carried out by employing a B3LYP hybrid functional using the Gaussian 03 program. Molecular orbitals were visualized by using GView. The 6-31G*+ basis set was used for C, N, O, and H atoms, and the effective core potential basis set LanL2DZ was used for the Zn atom. The geometry of 2 was taken from the crystal structure. 13Gaussian 03, Revision B.04, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. 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Switzer in Nitric Oxide Biology And Pathology (Eds.: ), Academic Press, New York, 2000, pp. 23– 40. 15 15aS. Goldstein, J. Lind, G. Merenyi, Chem. Rev. 2005, 105, 2457– 2470; 15bJ. S. Beckman, T. W. Beckman, J. Chen, P. A. Marshall, B. A. Freeman, Proc. Natl. Acad. Sci. USA 1990, 87, 1620– 1624. 16 16aJ. T. Groves, S. S. Marla, J. Am. Chem. Soc. 1995, 117, 9578– 9579; 16bM. K. Stern, M. P. Jensen, K. Kramer, J. Am. Chem. Soc. 1996, 118, 8735– 8736; 16cA. Mahammed, Z. Gross, Angew. Chem. 2006, 118, 6694– 6697; Angew. Chem. Int. Ed. 2006, 45, 6544– 6547; 16dZ. Okun, L. Kupershmidt, T. Amit, S. Mandel, O. Bar-Am, M. B. H. Youdim, Z Gross, ACS Chem. Biol. 2009, 4, 910– 914; 16eI. Aviv, Z. Gross, Chem. Commun. 2007, 1987– 1999. 17 17aB. Evans, K. M. Smith, Tetrahedron Lett. 1976, 17, 4863-. 4866; 17bB. Evans, K. M. Smith, J. A. S. Cavaleiro, J. Chem. Soc. Perkin Trans. 1 1978, 768– 773. 18 18aK. M. Smith, S. B. Brown, R. F. Troxler, J. J. Lai, Tetrahedron Lett. 1980, 21, 2763– 2766; 18bK. M. Smith, S. B. Brown, R. F. Troxler, J. J. Lai, Photochem. Photobiol. 1982, 36, 147-. 152; 18cR. F. Troxler, K. M. Smith, S. B. Brown, Tetrahedron Lett. 1980, 21, 491– 494. 19A. L. Balch, B. C. Noll, E. P. Zovinka, J. Am. Chem. Soc. 1992, 114, 3380– 3385. 20Under prolonged direct exposure of sunlight in the presence of air 2 degrades in toluene to a zinc biliverdin type complex along with several other unidentified products. Citing Literature Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description chem_201001073_sm_miscellaneous_information.pdf337.6 KB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume16, Issue35September 17, 2010Pages 10649-10652 ReferencesRelatedInformation
Publication Year: 2010
Publication Date: 2010-08-04
Language: en
Type: article
Indexed In: ['crossref', 'pubmed']
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