Crystal structure and solid-state NMR analysis of methyl 2,3,6-tri-O-acetyl-2-deoxy-2-[3-(2-phenylethyl)-ureido]-β-D-glucopyranoside

Carbohydrate Research

Volumn 281, Issue 1, 1996, Pages 1-10

  Anulewicz, Roma ^a   Wawer, Iwona ^a   Piekarska Bartoszewicz, Bogusława ^a   Temeriusz, Andrzej ^a  

^a UNIVERSITY OF WARSAW   (Poland)

Author keywords

13C CP mas solid state NMR; Crystal structure; Hydrogen bonding; Ureido sugars

Indexed keywords

CARBOHYDRATE DERIVATIVE;

ARTICLE; CARBOHYDRATE ANALYSIS; DRUG STRUCTURE; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; X RAY DIFFRACTION;

ANTINEOPLASTIC AGENTS; CRYSTALLOGRAPHY, X-RAY; GLUCOSIDES; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; UREA;

EID: 0030063688     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/0008-6215(95)00343-6     Document Type: Article

References (20)

1. B. Serrou, P.S. Schein, and J.L. Imbach (Eds.), Nitrosoureas in Cancer Treatments, Inserm Symposium No. 19, p 249, Elsevier, Amsterdam, 1981; B. Bannister, J. Antibiot., 25 (1972) 377-386; P.S. Schein, M.G. McMenamin, and T. Anderson, Cancer Res., 33 (1973) 2005-2009; J.J. Vavra, C. DeBoer, A. Dietz, L.J. Hanka, and W.T. Sokolski, Antibiot. Ann., (1959/1960) 230-235; R.R. Herr, H.K. Jahnke, and A.D. Argoudelis, J. Am. Chem. Soc., 89 (1967) 4808-4809; E.J. Hessler and H.K. Jahnke, J. Org. Chem., 35 (1970) 245-246; T.P. Johnston, G.S. McCaleb, and J.A. Montgomery, J. Med. Chem., 18 (1975) 104-106; T. Anderson, M.G. McMenamin, and P.S. Schein, Cancer Res., 35 (1975) 761-765.
2. B. Serrou, P.S. Schein, and J.L. Imbach (Eds.), Nitrosoureas in Cancer Treatments, Inserm Symposium No. 19, p 249, Elsevier, Amsterdam, 1981; B. Bannister, J. Antibiot., 25 (1972) 377-386; P.S. Schein, M.G. McMenamin, and T. Anderson, Cancer Res., 33 (1973) 2005-2009; J.J. Vavra, C. DeBoer, A. Dietz, L.J. Hanka, and W.T. Sokolski, Antibiot. Ann., (1959/1960) 230-235; R.R. Herr, H.K. Jahnke, and A.D. Argoudelis, J. Am. Chem. Soc., 89 (1967) 4808-4809; E.J. Hessler and H.K. Jahnke, J. Org. Chem., 35 (1970) 245-246; T.P. Johnston, G.S. McCaleb, and J.A. Montgomery, J. Med. Chem., 18 (1975) 104-106; T. Anderson, M.G. McMenamin, and P.S. Schein, Cancer Res., 35 (1975) 761-765.
3. B. Serrou, P.S. Schein, and J.L. Imbach (Eds.), Nitrosoureas in Cancer Treatments, Inserm Symposium No. 19, p 249, Elsevier, Amsterdam, 1981; B. Bannister, J. Antibiot., 25 (1972) 377-386; P.S. Schein, M.G. McMenamin, and T. Anderson, Cancer Res., 33 (1973) 2005-2009; J.J. Vavra, C. DeBoer, A. Dietz, L.J. Hanka, and W.T. Sokolski, Antibiot. Ann., (1959/1960) 230-235; R.R. Herr, H.K. Jahnke, and A.D. Argoudelis, J. Am. Chem. Soc., 89 (1967) 4808-4809; E.J. Hessler and H.K. Jahnke, J. Org. Chem., 35 (1970) 245-246; T.P. Johnston, G.S. McCaleb, and J.A. Montgomery, J. Med. Chem., 18 (1975) 104-106; T. Anderson, M.G. McMenamin, and P.S. Schein, Cancer Res., 35 (1975) 761-765.
4. B. Serrou, P.S. Schein, and J.L. Imbach (Eds.), Nitrosoureas in Cancer Treatments, Inserm Symposium No. 19, p 249, Elsevier, Amsterdam, 1981; B. Bannister, J. Antibiot., 25 (1972) 377-386; P.S. Schein, M.G. McMenamin, and T. Anderson, Cancer Res., 33 (1973) 2005-2009; J.J. Vavra, C. DeBoer, A. Dietz, L.J. Hanka, and W.T. Sokolski, Antibiot. Ann., (1959/1960) 230-235; R.R. Herr, H.K. Jahnke, and A.D. Argoudelis, J. Am. Chem. Soc., 89 (1967) 4808-4809; E.J. Hessler and H.K. Jahnke, J. Org. Chem., 35 (1970) 245-246; T.P. Johnston, G.S. McCaleb, and J.A. Montgomery, J. Med. Chem., 18 (1975) 104-106; T. Anderson, M.G. McMenamin, and P.S. Schein, Cancer Res., 35 (1975) 761-765.
5. B. Serrou, P.S. Schein, and J.L. Imbach (Eds.), Nitrosoureas in Cancer Treatments, Inserm Symposium No. 19, p 249, Elsevier, Amsterdam, 1981; B. Bannister, J. Antibiot., 25 (1972) 377-386; P.S. Schein, M.G. McMenamin, and T. Anderson, Cancer Res., 33 (1973) 2005-2009; J.J. Vavra, C. DeBoer, A. Dietz, L.J. Hanka, and W.T. Sokolski, Antibiot. Ann., (1959/1960) 230-235; R.R. Herr, H.K. Jahnke, and A.D. Argoudelis, J. Am. Chem. Soc., 89 (1967) 4808-4809; E.J. Hessler and H.K. Jahnke, J. Org. Chem., 35 (1970) 245-246; T.P. Johnston, G.S. McCaleb, and J.A. Montgomery, J. Med. Chem., 18 (1975) 104-106; T. Anderson, M.G. McMenamin, and P.S. Schein, Cancer Res., 35 (1975) 761-765.
6. B. Serrou, P.S. Schein, and J.L. Imbach (Eds.), Nitrosoureas in Cancer Treatments, Inserm Symposium No. 19, p 249, Elsevier, Amsterdam, 1981; B. Bannister, J. Antibiot., 25 (1972) 377-386; P.S. Schein, M.G. McMenamin, and T. Anderson, Cancer Res., 33 (1973) 2005-2009; J.J. Vavra, C. DeBoer, A. Dietz, L.J. Hanka, and W.T. Sokolski, Antibiot. Ann., (1959/1960) 230-235; R.R. Herr, H.K. Jahnke, and A.D. Argoudelis, J. Am. Chem. Soc., 89 (1967) 4808-4809; E.J. Hessler and H.K. Jahnke, J. Org. Chem., 35 (1970) 245-246; T.P. Johnston, G.S. McCaleb, and J.A. Montgomery, J. Med. Chem., 18 (1975) 104-106; T. Anderson, M.G. McMenamin, and P.S. Schein, Cancer Res., 35 (1975) 761-765.
7. B. Serrou, P.S. Schein, and J.L. Imbach (Eds.), Nitrosoureas in Cancer Treatments, Inserm Symposium No. 19, p 249, Elsevier, Amsterdam, 1981; B. Bannister, J. Antibiot., 25 (1972) 377-386; P.S. Schein, M.G. McMenamin, and T. Anderson, Cancer Res., 33 (1973) 2005-2009; J.J. Vavra, C. DeBoer, A. Dietz, L.J. Hanka, and W.T. Sokolski, Antibiot. Ann., (1959/1960) 230-235; R.R. Herr, H.K. Jahnke, and A.D. Argoudelis, J. Am. Chem. Soc., 89 (1967) 4808-4809; E.J. Hessler and H.K. Jahnke, J. Org. Chem., 35 (1970) 245-246; T.P. Johnston, G.S. McCaleb, and J.A. Montgomery, J. Med. Chem., 18 (1975) 104-106; T. Anderson, M.G. McMenamin, and P.S. Schein, Cancer Res., 35 (1975) 761-765.
8. B. Serrou, P.S. Schein, and J.L. Imbach (Eds.), Nitrosoureas in Cancer Treatments, Inserm Symposium No. 19, p 249, Elsevier, Amsterdam, 1981; B. Bannister, J. Antibiot., 25 (1972) 377-386; P.S. Schein, M.G. McMenamin, and T. Anderson, Cancer Res., 33 (1973) 2005-2009; J.J. Vavra, C. DeBoer, A. Dietz, L.J. Hanka, and W.T. Sokolski, Antibiot. Ann., (1959/1960) 230-235; R.R. Herr, H.K. Jahnke, and A.D. Argoudelis, J. Am. Chem. Soc., 89 (1967) 4808-4809; E.J. Hessler and H.K. Jahnke, J. Org. Chem., 35 (1970) 245-246; T.P. Johnston, G.S. McCaleb, and J.A. Montgomery, J. Med. Chem., 18 (1975) 104-106; T. Anderson, M.G. McMenamin, and P.S. Schein, Cancer Res., 35 (1975) 761-765.
9. I. Wawer, B. Piekarska-Bartoszewicz, and A. Temeriusz, Carbohydr. Res., 267 (1995) 167-176.
10. G.A. Jeffrey, R.A. Wood, P.E. Pfeffer, and K.B. Hicks, J. Am. Chem. Soc., 105 (1983) 2128-2133.
11. G.M. Sheldrick, SHELXL93, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1993.
12. D. Cremer and J.A. Pople, J. Am. Chem. Soc., 97 (1975) 1354-1358.
13. J.D. Oliver and L.C. Strickland, Acta Crystallogr., Sect. B, 40 (1984) 820-824.
14. T. Taga, S. Sumiya, K. Osaki, T. Utamura, and K. Koizumi, Acta Crystallogr., Sect. B, 37 (1981) 963-966.
15. C. Toniolo, G. Valle, G.M. Bonora, M. Crisma, V. Moretto, J. Izdebski, J. Pelłka, D. Pawlak, and C.H. Schneider, Int. J. Peptide Protein Res., 31 (1988) 77-85.
16. W.A. Brett, P. Rademacher, and R. Boese, Acta Crystallogr., Sect. C, 46 (1990) 880-882.
17. S. Ando, I. Ando, A. Shoji, and T. Ozaki, J. Am. Chem. Soc., 110 (1988) 3380-3386.
18. B. Piekarska-Bartoszewicz and A. Temeriusz, Carbohydr. Res., 204 (1990) 302-307.
19. G.M. Sheldrick, Acta Crystallogr., Sect. A, 46 (1990) 467-473.
20. International Tables for X-ray Crystallography, Vol. IV, Kynoch, Birmingham, 1974 (present distributor: Kluwer Academic Publishers, Amsterdam).