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<title>UTas ePrints - Heavy-Metal-Nucleoside Interactions. 13. Synthesis and Spectroscopic Study of Organomercury Derivatives of Guanosine and Thymidine</title>
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<meta content="Canty, A.J." name="eprints.creators_name" />
<meta content="Tobias, R.S." name="eprints.creators_name" />
<meta content="allan.canty@utas.edu.au" name="eprints.creators_id" />
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<meta content="Complexes of the stoichiometry RHg(GuoH-1), [RHg(Guo)]N03, and [(RHg)2GUOH-1]NO3 have been synthesized by reaction of the nucleoside guanosine (Guo) and RHg(II) in water (R = Me) or aqueous ethanol (R = Ph). Comparison of infrared spectra of the solid complexes and 1H nuclear magnetic resonance spectra of the complexes in dimethyl-d6 sulfoxide
with spectra of Guo, [GuoH]N03, and Na[GuoH-1].H20 allows assignment of structures for these ambidentate ligand
complexes. Deprotonation of N1 of Guo leads to coordination of RHg(II) at N1 in RHg(GuoH-1) and to both N1 and N7 in [(RHg)2GuoH-l]N03. The complexes [RHg(Guo)]N03 have RHg(II) bonded at N7 of the guanine base. Phenylmercuric hydroxide reacts with thymidine (dThd) in aqueous ethanol to form PhHg(dThdH-1).H20 with PhHg(II) bonded to N3 after deprotonation of dThd. Structures deduced for these solid complexes are in agreement with those suggested in earlier ultraviolet and Raman studies of the interaction of nucleosides and nucleotides with MeHg(II) in aqueous solution. The uses and limitations
of vibrational spectra in assigning structures to such metal nucleoside complexes are outlined." name="eprints.abstract" />
<meta content="1979" name="eprints.date" />
<meta content="published" name="eprints.date_type" />
<meta content="Inorganic Chemistry" name="eprints.publication" />
<meta content="18" name="eprints.volume" />
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<meta content="413-417" name="eprints.pagerange" />
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(1) Work supported by US. Public Health Service Grant AM 16101 from
the National Institute for Arthritis, Metabolism, and Digestive Diseases
and by the National Science Foundation, Grant MPS 73-04856.
(2) Part 12: S. Mansy, G. Y. H. Chu, R. E. Duncan, and R. S. Tobias, J.
Am. Chem. Soc., 100, 607 (1978).
(3) Fulbright Senior Scholar. On leave from the University of Tasmania,
Hobart, Tasmania, Australia.
(4) (a) J. M. Bailey and N. Davidson, Anal Biochem., 70,75 (1976); (b)
U. S. Nandi, J. C. Wang, and N Davidson, BLochemrstry, 4, 1687 (1965);
Inorganic Chemistry, Vol. 18, No. 2, 1979 417
(c) N. Davidson, J. Widholm, U. S. Nandi, R. Jensen, B. M. Olivera,
and J. C. Wang, Proc. Natl. Acad. Sci. U.S.A., 53, 111 (1965).
D. L. Rabenstein, Acc. Chem. Res., 11, 100 (1978).
(a) S. Mansy, T. E. Wood, J. C. Sprowles, and R. S. Tobias, J. Am.
Chem. Soc., 96, 1762 (1974); (b) S. Mansy and R. S. Tobias, ibid.,
96, 6874 (1974).
S. Mansy, J. P. Frick, and R. S. Tobias, Biochim. Biophys. Acta, 378,
319 (1975).
S. Mansy and R. S. Tobias, Biochemistry, 14, 2952 (1975).
R. W. Chrisman, S. Mansy, H. J. Peresie, A. Ranade, T. A. Berg, and
R. S. Tobias, Bioinorg. Chem., 7, 245 (1977).
(a) G. Y. H. Chu and R. S. Tobias, J. Am. Chem. Soc., 98,2641 (1976);
(b) G. Y. H. Chu, R. E. Duncan, and R. S. Tobias, Inorg. Chem., 16,
2625 (1977).
G. Y. H. Chu, S. Mansy, R. E. Duncan, and R. S. Tobias, J. Am. Chem.
Soc., 100, 593 (1978):
D. W. Gruenwedel and N. Davidson, J. Mol. Biol., 21. 129 (1966).
The IUPAC-IUB abbreviations for nucleosides, etc., are employed
throughout; see Biochemistry, 9, 4022 (1970).
R. B. Simpson, J. Am. Chem Soc., 86, 2059 (1964).
C. C. Addison, N. Logan, S. C. Wallwork, and C. D. Garner, Chem.
SOC. Rev., 25, 289 (1971).
(a) A. J. Canty and B. M. Gatehouse, J. Chem. SOC.D, alton Trans.,
2018 (1976); (b) A. J. Canty, M. Fyfe, and B. M. Gatehouse, Inorg.
Chem., 17, 1467 (1978).
M. Tsuboi, Y. Kyogoku, and T. Shimanouchi, Biochim. Biophys. Acta,
55, 1 (1962).
C. L. Angell, J. Chem. SOC., 504 (1961).
H. T. Miles, F. B. Howard, and J. Frazier, Science, 142, 1458 (1963).
R. C. Lord and G. J. Thomas, Jr., Spectrochim. Acta, Part A, 23a, 2551
(1967).
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G. Pneumatikakis, N. Hadjiliadis, and T. Theophanides, Inorg. Chem.,
17, 915 (1978).
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J Iball and H. R. Wilson, Proc. R. SOC. London, 288, 418 (1965).
(a) F. A. L. Anet and J. L. Sudmeier, J. Magn. Reson., 1, 124 (1969);
(b) H. F. Henneike, J. Am. Chem. SOC.9, 4, 5945 (1972).
R. M. Izatt, J. J. Christensen, and J. H. Rytting, Chem. Rev., 71, 439
(1 971). i. W. Erni, Ph.D. Dissertation, E.T.H., Zurich, 1977.
(a) A. J. Canty and A. Marker, Inorg. Chem., 15,425 (1976); (b) A.
J. Canty, A. Marker, P. Barron, and P. C. Healy, J. Organomet. Chem.,
144, 371 (1978)." name="eprints.referencetext" />
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<meta content="Complexes of the stoichiometry RHg(GuoH-1), [RHg(Guo)]N03, and [(RHg)2GUOH-1]NO3 have been synthesized by reaction of the nucleoside guanosine (Guo) and RHg(II) in water (R = Me) or aqueous ethanol (R = Ph). Comparison of infrared spectra of the solid complexes and 1H nuclear magnetic resonance spectra of the complexes in dimethyl-d6 sulfoxide
with spectra of Guo, [GuoH]N03, and Na[GuoH-1].H20 allows assignment of structures for these ambidentate ligand
complexes. Deprotonation of N1 of Guo leads to coordination of RHg(II) at N1 in RHg(GuoH-1) and to both N1 and N7 in [(RHg)2GuoH-l]N03. The complexes [RHg(Guo)]N03 have RHg(II) bonded at N7 of the guanine base. Phenylmercuric hydroxide reacts with thymidine (dThd) in aqueous ethanol to form PhHg(dThdH-1).H20 with PhHg(II) bonded to N3 after deprotonation of dThd. Structures deduced for these solid complexes are in agreement with those suggested in earlier ultraviolet and Raman studies of the interaction of nucleosides and nucleotides with MeHg(II) in aqueous solution. The uses and limitations
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<h1 class="ep_tm_pagetitle">Heavy-Metal-Nucleoside Interactions. 13. Synthesis and Spectroscopic Study of Organomercury Derivatives of Guanosine and Thymidine</h1>
<p style="margin-bottom: 1em" class="not_ep_block"><span class="person_name">Canty, A.J.</span> and <span class="person_name">Tobias, R.S.</span> (1979) <xhtml:em>Heavy-Metal-Nucleoside Interactions. 13. Synthesis and Spectroscopic Study of Organomercury Derivatives of Guanosine and Thymidine.</xhtml:em> Inorganic Chemistry, 18 (2). pp. 413-417. ISSN 0020-1669</p><p style="margin-bottom: 1em" class="not_ep_block"></p><table style="margin-bottom: 1em" class="not_ep_block"><tr><td valign="top" style="text-align:center"><a href="http://eprints.utas.edu.au/2861/1/IC1979_2C_413.pdf"><img alt="[img]" src="http://eprints.utas.edu.au/style/images/fileicons/application_pdf.png" border="0" class="ep_doc_icon" /></a></td><td valign="top"><a href="http://eprints.utas.edu.au/2861/1/IC1979_2C_413.pdf"><span class="ep_document_citation">PDF</span></a> - Full text restricted - Requires a PDF viewer<br />694Kb</td><td><form method="get" accept-charset="utf-8" action="http://eprints.utas.edu.au/cgi/request_doc"><input value="4081" name="docid" accept-charset="utf-8" type="hidden" /><div class=""><input value="Request a copy" name="_action_null" class="ep_form_action_button" onclick="return EPJS_button_pushed( '_action_null' )" type="submit" /> </div></form></td></tr></table><p style="margin-bottom: 1em" class="not_ep_block">Official URL: <a href="http://dx.doi.org/10.1021/ic50192a044">http://dx.doi.org/10.1021/ic50192a044</a></p><div class="not_ep_block"><h2>Abstract</h2><p style="padding-bottom: 16px; text-align: left; margin: 1em auto 0em auto">Complexes of the stoichiometry RHg(GuoH-1), [RHg(Guo)]N03, and [(RHg)2GUOH-1]NO3 have been synthesized by reaction of the nucleoside guanosine (Guo) and RHg(II) in water (R = Me) or aqueous ethanol (R = Ph). Comparison of infrared spectra of the solid complexes and 1H nuclear magnetic resonance spectra of the complexes in dimethyl-d6 sulfoxide
with spectra of Guo, [GuoH]N03, and Na[GuoH-1].H20 allows assignment of structures for these ambidentate ligand
complexes. Deprotonation of N1 of Guo leads to coordination of RHg(II) at N1 in RHg(GuoH-1) and to both N1 and N7 in [(RHg)2GuoH-l]N03. The complexes [RHg(Guo)]N03 have RHg(II) bonded at N7 of the guanine base. Phenylmercuric hydroxide reacts with thymidine (dThd) in aqueous ethanol to form PhHg(dThdH-1).H20 with PhHg(II) bonded to N3 after deprotonation of dThd. Structures deduced for these solid complexes are in agreement with those suggested in earlier ultraviolet and Raman studies of the interaction of nucleosides and nucleotides with MeHg(II) in aqueous solution. The uses and limitations
of vibrational spectra in assigning structures to such metal nucleoside complexes are outlined.</p></div><table style="margin-bottom: 1em" border="0" cellpadding="3" class="not_ep_block"><tr><th valign="top" class="ep_row">Item Type:</th><td valign="top" class="ep_row">Article</td></tr><tr><th valign="top" class="ep_row">Subjects:</th><td valign="top" class="ep_row"><a href="http://eprints.utas.edu.au/view/subjects/250204.html">250000 Chemical Sciences > 250200 Inorganic Chemistry > 250204 Bioinorganic Chemistry</a></td></tr><tr><th valign="top" class="ep_row">ID Code:</th><td valign="top" class="ep_row">2861</td></tr><tr><th valign="top" class="ep_row">Deposited By:</th><td valign="top" class="ep_row"><span class="ep_name_citation"><span class="person_name">Prof Allan J Canty</span></span></td></tr><tr><th valign="top" class="ep_row">Deposited On:</th><td valign="top" class="ep_row">14 Jan 2008 13:55</td></tr><tr><th valign="top" class="ep_row">Last Modified:</th><td valign="top" class="ep_row">14 Jan 2008 13:55</td></tr><tr><th valign="top" class="ep_row">ePrint Statistics:</th><td valign="top" class="ep_row"><a target="ePrintStats" href="/es/index.php?action=show_detail_eprint;id=2861;">View statistics for this ePrint</a></td></tr></table><p align="right">Repository Staff Only: <a href="http://eprints.utas.edu.au/cgi/users/home?screen=EPrint::View&eprintid=2861">item control page</a></p>
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