1H, 13C, and 15N NMR Study of Nitrosoureido Sugars, Derivatives of 2-Amino-2-deoxy-beta=D-glucopyranoside and Amino Acids or Peptides

• Autorzy: Wawer I. , Weychert M. , Piekarska-Bartoszewicz B. , Temeriusz A.
• Języki publikacji: EN

Abstrakty

EN

Nitrosoureido sugars with amino acid and dipeptide ester residue were characterized by 1H, 13C and 15N NMR and their spectra were assigned using 1D and 2D NMR methods. The N-nitrosation of ureido sugars frequently yields a mixture of isomers. In the case of ureido sugars with amino acid residues preferably the N3-NO isomers were obtained, whereas for compounds with dipeptide esters the N1-NO isomers dominate. The results are in agreement with the molecular modelling (PM3) predictions, when the intramolecular hydrogen bonds, net charges at nitrogen atoms and heat of formations of particular isomers are considered.

Słowa kluczowe

EN

NMR spectroscopy; antitumor agents; nitrosoureido sugars

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2002
• Tom: Vol. 76 / nr 8
• Strony: 1127--1136
• Opis fizyczny: Bibliogr. 14 poz., rys.

Twórcy

autor

Wawer I.

• Faculty of Pharmacy, Medical University of Warsaw, Banacha 1, 02097 Warsaw, Poland

autor

Weychert M.

• Faculty of Pharmacy, Medical University of Warsaw, Banacha 1, 02097 Warsaw, Poland

autor

Piekarska-Bartoszewicz B.

• 1Department of Chemistry, Warsaw University, Pasteura 1, 02093 Warsaw, Poland

autor

Temeriusz A.

• 1Department of Chemistry, Warsaw University, Pasteura 1, 02093 Warsaw, Poland

Bibliografia

• 1. Gnewuch C.T. and Sosnowsky G., Chem. Rev., 97, 829 (1997).
• 2. Lin T.S., Fischer P.H., Shiau G.T. and Prusoff W.H., J. Am. Chem. Soc., 21,130 (197S).
• 3. Johnston T.P., McCaleb G.S., Opliger P.S. and Montgomery J.A., J. Med. Chem., 9, 892 (1966).
• 4. Johnston T.P., McCaleb G.S. and Montgomery J.A., J. Med. Chem., 18, 104 (1975).
• 5. Lown J.W. and Chauhan S.M.S., J. Org. Chem., 48, 507 (1983),
• 6. Plass M., Wawer I., Piekarska-Bartoszewicz B. and Temeriusz A., J. Phys. Organ. Chem., 10, 747 (1997).
• 19, Plass M., Weychert M., Wawer I., Piekarska-Bartoszewicz B. and Temeriusz A., J. Carbohydr. Chem.,1059 (2000),
• 7. Temeriusz A,, Piekarska-Bartoszewicz B., Weychert M. and. Wawer I„ Polish J. Chem., 73, 1011 (1999).
• 8. Wawer I., Piekarska-Bartoszewicz B. and Temeriusz A., Carbohydr. Res., 279, 83 (1995); Temeriusz A., Piekarska-Bartoszewicz B. and Wawer I., Carbohydr. Res., 304, 334 (1997).
• 9. Weychert M., Klimkiewicz J., Wawer 1,, Piekarska-Bartoszewicz B. and Temeriusz A., Magn. Reson. Chem., 36,727(1998).
• 10. Witanowski M., Stefaniak L. and Webb G.A., Ann. Rep. NMR Spectroscop., 25,382 (1992).
• 11. Piekarska-Bartoszewicz B. and Temeriusz A., J. Carbohydr. Chem., 12, 913 (1993); Temeriusz A., Piekarska-Bartoszewicz B. and Wawer I., Carbohydr. Res., 304,334 (1997).
• 12. HyperChem 5.02 package, Hypercube Inc., Canada 1997.
• 13. Steward J.J.P., J. Comput. Chem., 10,221 (1989).