Stereochemistry of platinum complexes of the neutral amino acids allylglycine, S-methylcysteine, methionine, and corresponding sulfoxides

Inorganica Chimica Acta

Volumn 346, Issue , 2003, Pages 169-180

  Erickson, Luther E ^a   Bailey, Paul D ^a   Kimball, Todd L ^a   Morgan, Benjamin R ^a  

^a GRINNELL COLLEGE   (United States)

Author keywords

Amino acid; Chelate; Conformation; NMR; Platinum; Stereochemistry

Indexed keywords

AMINO ACIDS; CHELATION; CONFORMATIONS; ISOMERS; MOLECULAR MECHANICS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANTS (BOTANY); PLATINUM; PLATINUM COMPOUNDS; STEREOCHEMISTRY; STEREOSELECTIVITY; X RAYS;

CHELATE; CHELATE RING CONFORMATION; LOW-ENERGY CONFORMATIONS; METHIONINE SULFOXIDE; MOLECULAR MECHANICS CALCULATIONS; PROTON NMR SPECTROSCOPY; PROTON-PROTON COUPLING CONSTANTS; SQUARE PLANAR COMPLEX;

X RAY CRYSTALLOGRAPHY;

ALLYLGLYCINE; METHIONINE; PLATINUM COMPLEX; S METHYLCYSTEINE; SULFOXIDE;

ARTICLE; BINDING SITE; CALCULATION; CRYSTAL STRUCTURE; DIASTEREOISOMER; KINETICS; MOLECULAR DYNAMICS; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0037465626     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0020-1693(02)01461-5     Document Type: Article

References (25)

1. Erickson L.E., Morris K.F., Panajotova B.V., Jiang D.W., Ding F. Inorg. Chem. 36:1997;601.
2. Steiner N., Nagel U., Beck W. Chem. Ber. 121:1988;1759.
3. This cis and trans designation of configuration will be used throughout our discussion of complexes of the sulfur containing amino acids to avoid possible confusion associated with changing R, S descriptions resulting from bonding the free amino acid S atom to Pt.
4. Clow R.P., Erickson L.E., Howie J.K., McDonald J.W. J. Am. Chem. Soc. 90:1968;6371.
5. Gummin D.D., Ratilla E.M.A., Kostic N.M. Inorg. Chem. 25:1986;2429.
6. Theodorou V., Photake I., Hadjiliadis N., Gellert R.W., Bau R. Inorg. Chim. Acta. 60:1982;1.
7. Battaglia L.P., Corradi A.B., Palmieri C.G., Nardelli M., Tani M.E.V. Acta Crystallogr., B. 29:1973;762.
8. H.C. Freeman, M.L. Golomb, Chem. Commun. (1970) 1523.
9. Nicholls L.J., Freeman W.A. Acta Crystallogr., B. 35:1979;2392.
10. Slyudkin O.P., Baidina I.A., Dolbina L.N. Russ. J. Coord. Chem. 23:1997;401.
11. Freeman W.A. Acta Crystallogr., B. 33:1977;191.
12. Slyudkin O.P. Russ. J. Coord. Chem. 23:1997;407.
13. Hartley F.R. The Chemistry of Platinum and Palladium. 1973;99 Wiley, New York.
14. Software from Universidade de Santiago de Compostela; available on-line at http://www.sif.iisc.ernet.in/mes.htm.
15. Data Collection: SMART Software Reference Manual (1994). Bruker-AXS, Madison, WI, USA. Data Reduction: SAINT Software Reference Manual (1995). Bruker-AXS, 6300 Enterprise Dr., Madison, WI 53719-1173, USA.
16. Sheldrick G.M. SADABS. Program for Empirical Absorption Correction of Area Detector Data. 1996;University of Göttingen, Göttingen, Germany.
17. G.M. Sheldrick, SHELXTL Version 5 Reference Manual, Bruker-AXS, Madison, WI, 1994. International Tables for Crystallography, Vol. C, Tables 6.1.1.4, 4.2.6.8, and 4.2.4.2, Kluwer, Boston (1995).
18. From the CACHE Group, Fujitsu, Beaverton, OR; http://www.CACheSoftware.com.
19. Karplus M. J. Chem. Phys. 30:1959;11.
20. Karplus M. J. Am. Chem. Soc. 85:1963;2870.
21. Haasnoot C.A.G., de Leeuf F.A., Altona C. Tetrahedron. 36:1980;2783.
22. Erickson L.E., Erickson M., Smith B. Inorg. Chem. 12:1973;412.
23. Ahmed K.J., Blanchard J.L., Erickson L.E., Jones G.S. Inorg. Chem. 30:1991;3147.
24. The change in designation of configuration at the sulfur atom again reflects the replacement of Pt by the lone-pair of the free amino acid; there is no evidence of any change in configuration at S on displacement of the ligand from the complex by CN-.
25. Standard chelate ring conformation nomenclature, See S.V. Zelewsky, Stereochemistry of Coordination Compounds, Wiley, New York, p. 111.