31P High Resolution solid State NMR Studies of Phosphoroorganic Compounds of Biological Interest

• Autorzy: Potrzebowski M. , Ganicz K. , Kaźmierski S.
• Języki publikacji: EN

Abstrakty

EN

In this review several applications of 31P high resolution solid state NMR spectroscopy in structural studies of bioorganic samples is reported. The problem of pseudopolymorphism of bis[6-O,6_-O-(1,2:3,4-diisopropylidene-_-D-galactopyranosyl) phosphorothioyl] disulfide 1 and application of 31P CP/MAS experiment to investigate of this phenomenon is discussed. The influence of weak C-H___S intermolecular contacts on molecular packing of 1,6-anhydro-2-O-tosyl-4-S-(5,5-dimethyl-2-thioxa-1,3,2-dioxaphosphorinan-2-yl)- _-D-glucopyranose 2 and SP, RP diastereomers of deoxyxylothymidyl-3_-O-acetylthymidyl (3_,5_)-O-(2-cyanoethyl) phosphorothioate 3 and their implication on 31P NMR spectra is shown. The final part of review describes the recent progress in structural studies of O-phosphorylated amino acids (serine, threonine, tyrosine), relationship between molecular structure and 31P chemical shift parameters _ii and influence of hydrogen bonding on values of principal elements of chemical shift tensor.

Słowa kluczowe

EN

structural studies; solid state NMR; pseudopolymorphism; intermolecular contacts; carbohydrate derivatives; phosphorylated amino acids; chemical shift tensor; hydrogen bonding

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2001
• Tom: Vol. 75, nr 8
• Strony: 1147--1169
• Opis fizyczny: Bibliogr. 37 poz., rys.

Twórcy

autor

Potrzebowski M.

• Polish Academy of Sciences, Center of Molecular and Macromolecular Studies, Sienkiewicza 112, 90-363 Lódź, Poland

autor

Ganicz K.

• Polish Academy of Sciences, Center of Molecular and Macromolecular Studies, Sienkiewicza 112, 90-363 Lódź, Poland

autor

Kaźmierski S.

• Polish Academy of Sciences, Center of Molecular and Macromolecular Studies, Sienkiewicza 112, 90-363 Lódź, Poland

Bibliografia

• 1.Fyfe C.A., Solid State NMR for Chemists, Eds. CFC Press, Guelph, Ontario 1983.
• 2.Mehring M., Principles of High Resolution NMR in Solids, Springer, Berlin 1983.
• 3.Yannoni C.S., Acc. Chem. Res., 15, 201 (1982).
• 4.Schaefer J. and Stejskal E.O., J. Am. Chem. Soc., 98, 1031 (1976).
• 5.Gorenstein D.G., Phosphorus-31 NMR. Principles and Applications, Academic Press, Orlando 1984.
• 6.Van Wazer J.R., Phosphorus and its Compounds, Intersc. Publ., NY 1961.
• 7.Verkade J.G. and Quin L.D., Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis, VCH Publ. Inc., Deerfield Beach 1987.
• 8.Glusker J.P., Lewis M. and Rossi M., Crystal Structure Analysis for Chemists and Biologists, VCH Publishers, Inc., NY 1994, p. 44.
• 9.Kumar V.S.S., Kuduva S.S. and Desiraju G.R., J. Chem. Soc., Perkin Trans., 2, 1069 (1999).
• 10.Potrzebowski M.J., Blaszczyk J. and Wieczorek M.W., J. Org. Chem., 60, 2549 (1995).
• 11.Potrzebowski M.J., Ganicz K., Ciesielski W., Skowrońska A., Wieczorek M.W., Blaszczyk J. and Majzner W., J. Chem. Soc., Perkin Trans., 2, 2163 (1999).
• 12.Sutor D.J., Nature, 68, 195 (1962).
• 13.Sutor D.J.,Chem Soc., 1105 (1963).
• 14.Desiraju G.R., Angew. Chem., Int. Ed. Engl, 34, 2311 (1995).
• 15.Taylor R. and Kennard O., J. Am. Chem. Soc.. 104, 5063 (1982).
• 16.Desiraju G.R., Acc. Chem. Res., 24, 290 (1991).
• 17.Desiraju G.R., Acc. Chem. Res., 29, 441 (1996).
• 18.Auffinger P., Louise-May S. and Westhof E., J. Am. Chem. Soc., 118, 1181 (1996).
• 19.Novoa J.J., Carme Rovira M., Rovira C. and Veciane J. Tarres, J. Adv. Mater., 7, 233 (1995).
• 20.Borrmann H., Persson I., Sandström M. and Stälhandske Ch.M.V., J. Chem. Soc., Perkin Trans., 2, 393 (2000).
• 21.Potrzebowski M.J., Michalska M., Kozioł A.E., Kaźmierski S., Lis T., Pluskowski J. and Ciesielski W., J. Org. Chem., 63,4209 (1998).
• 22.WIN-MAS program, version 940108, Bruker-Franzen Analytik GMBH, Bremen 1994.
• 23.Herzfeld J. and Berger A., J. Chem. Phys., 73, 6021 (1980); Jeschke G. and Grossmann G., J. Magn. Reson., 12A103, 323 (1993).
• 24.Potrzebowski M.J. and Michalski J., Phosphorus-31 NMR Spectral Properties in Compound Characterization and Structural 12Analysis, Eds. L.D. Quin, J.G. Verkade, VCH 1994, p. 413.
• 25.Grossmann G., Beckmann H., Rademacher O., Krueger K. and Ohms G., J. Chem. Soc., Dalton Trans., 2797(1995).
• 26.Potrzebowski M.J., J. Chem. Soc., Perkin Trans., 2, 63 (1993).
• 27.Krüger K., Grossmann G., Fleischer U., Franke R. and Kutzelnigg W., Magn. Reson. Chem., 33 (1995).
• 28.Potrzebowski M.J., Yang X., Misiura K., Majzner W.R., Wieczorek M. W., Kaźmierski S., Olejniczak S. and Stec W.J., Eur. J Org. Chem., 1491 (2001).
• 29.Carroll M.T. and Bader R.F.W., Mol. Phys., 65, 695 (1988).
• 30.Braga D., Grepioni F., Biradha K., Pedireddi V.R. and Desiraju G.R., J. Am. Chem. Soc., 117, 3156 (1995).
• 31.Corbridge D.E.C., Phosphorus, An Outline of Its Chemistry, Biochemistry and Technology, Elsevier, Amsterdam-Oxford-New York-Tokyo, 1990, p. 880.
• 32.Marseigne I. and Rogues B.P., J. Org. Chem., 53,3621 (1988);Kitas E.A., Perich J.W.,Tregear G.W. and Johns R.B„J. Org. Chem., 55, 4181 (1990).
• 33.Putkey E. and Sundaralingam M., Acta Cryst., B26, 782 (1970).
• 34.Putkey E. and Sundaralingam M., Acta Cryst., B26, 790 (1970).
• 35.Maniukicwicz W., Kwiatkowski W. and Blessing R.H., Acta Cryst., C52, 1736 (1996).
• 36.Suga T., Inubushi C. and Okabe N., Acta Cryst., C54, 83 (1998).
• 37.Un S. and Klein M.P., J.Am. Chem. Soc., 111, 5119(1989).