Crystal structure and solid state NMR analysis of N-(methyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside)-N′-carbamoyl- D-valine ethyl ester

Journal of Carbohydrate Chemistry

Volumn 16, Issue 6, 1997, Pages 739-749

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

^a UNIVERSITY OF WARSAW   (Poland)

^b MEDICAL UNIVERSITY OF WARSAW   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001148570     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328309708006538     Document Type: Article

References (18)

1. B. Serrou, P.S. Schein and J.L. Imbach, Eds., Nitrosoureas in Cancer Treatment, Inserm Symposium No 19, pp 249. Elsevier, Amsterdam 1981; B. Bannister, J. Antibiot., 25, 377 (1972) ; P.S. Schein, M.G. McMenamin and T. Anderson, Cancer Res., 33, 2005 (1973); J.J. Vavra, C. DeBoer, A. Dietz, L.J. Hanka and W.T. Sokolski, Antibiot. Ann. 1959/1960, 230, R.R. Herr, H.K. Jahnke and A.D. Argoudelis, J. Am. Chem. Soc., 89, 4808 (1967); E.J. Hessler and H.K. Jahnke, J. Org. Chem., 35, 245 (1970); T.P. Johnston, G.S. McCaleb and J.A. Montgomery, J. Med. Chem., 18, 104 (1975); T. Anderson, M.G. McMenamin and P.S. Schein, Cancer Res., 35, 761 1975).
2. B. Serrou, P.S. Schein and J.L. Imbach, Eds., Nitrosoureas in Cancer Treatment, Inserm Symposium No 19, pp 249. Elsevier, Amsterdam 1981; B. Bannister, J. Antibiot., 25, 377 (1972) ; P.S. Schein, M.G. McMenamin and T. Anderson, Cancer Res., 33, 2005 (1973); J.J. Vavra, C. DeBoer, A. Dietz, L.J. Hanka and W.T. Sokolski, Antibiot. Ann. 1959/1960, 230, R.R. Herr, H.K. Jahnke and A.D. Argoudelis, J. Am. Chem. Soc., 89, 4808 (1967); E.J. Hessler and H.K. Jahnke, J. Org. Chem., 35, 245 (1970); T.P. Johnston, G.S. McCaleb and J.A. Montgomery, J. Med. Chem., 18, 104 (1975); T. Anderson, M.G. McMenamin and P.S. Schein, Cancer Res., 35, 761 1975).
3. B. Serrou, P.S. Schein and J.L. Imbach, Eds., Nitrosoureas in Cancer Treatment, Inserm Symposium No 19, pp 249. Elsevier, Amsterdam 1981; B. Bannister, J. Antibiot., 25, 377 (1972) ; P.S. Schein, M.G. McMenamin and T. Anderson, Cancer Res., 33, 2005 (1973); J.J. Vavra, C. DeBoer, A. Dietz, L.J. Hanka and W.T. Sokolski, Antibiot. Ann. 1959/1960, 230, R.R. Herr, H.K. Jahnke and A.D. Argoudelis, J. Am. Chem. Soc., 89, 4808 (1967); E.J. Hessler and H.K. Jahnke, J. Org. Chem., 35, 245 (1970); T.P. Johnston, G.S. McCaleb and J.A. Montgomery, J. Med. Chem., 18, 104 (1975); T. Anderson, M.G. McMenamin and P.S. Schein, Cancer Res., 35, 761 1975).
4. B. Serrou, P.S. Schein and J.L. Imbach, Eds., Nitrosoureas in Cancer Treatment, Inserm Symposium No 19, pp 249. Elsevier, Amsterdam 1981; B. Bannister, J. Antibiot., 25, 377 (1972) ; P.S. Schein, M.G. McMenamin and T. Anderson, Cancer Res., 33, 2005 (1973); J.J. Vavra, C. DeBoer, A. Dietz, L.J. Hanka and W.T. Sokolski, Antibiot. Ann. 1959/1960, 230, R.R. Herr, H.K. Jahnke and A.D. Argoudelis, J. Am. Chem. Soc., 89, 4808 (1967); E.J. Hessler and H.K. Jahnke, J. Org. Chem., 35, 245 (1970); T.P. Johnston, G.S. McCaleb and J.A. Montgomery, J. Med. Chem., 18, 104 (1975); T. Anderson, M.G. McMenamin and P.S. Schein, Cancer Res., 35, 761 1975).
5. B. Serrou, P.S. Schein and J.L. Imbach, Eds., Nitrosoureas in Cancer Treatment, Inserm Symposium No 19, pp 249. Elsevier, Amsterdam 1981; B. Bannister, J. Antibiot., 25, 377 (1972) ; P.S. Schein, M.G. McMenamin and T. Anderson, Cancer Res., 33, 2005 (1973); J.J. Vavra, C. DeBoer, A. Dietz, L.J. Hanka and W.T. Sokolski, Antibiot. Ann. 1959/1960, 230, R.R. Herr, H.K. Jahnke and A.D. Argoudelis, J. Am. Chem. Soc., 89, 4808 (1967); E.J. Hessler and H.K. Jahnke, J. Org. Chem., 35, 245 (1970); T.P. Johnston, G.S. McCaleb and J.A. Montgomery, J. Med. Chem., 18, 104 (1975); T. Anderson, M.G. McMenamin and P.S. Schein, Cancer Res., 35, 761 1975).
6. B. Serrou, P.S. Schein and J.L. Imbach, Eds., Nitrosoureas in Cancer Treatment, Inserm Symposium No 19, pp 249. Elsevier, Amsterdam 1981; B. Bannister, J. Antibiot., 25, 377 (1972) ; P.S. Schein, M.G. McMenamin and T. Anderson, Cancer Res., 33, 2005 (1973); J.J. Vavra, C. DeBoer, A. Dietz, L.J. Hanka and W.T. Sokolski, Antibiot. Ann. 1959/1960, 230, R.R. Herr, H.K. Jahnke and A.D. Argoudelis, J. Am. Chem. Soc., 89, 4808 (1967); E.J. Hessler and H.K. Jahnke, J. Org. Chem., 35, 245 (1970); T.P. Johnston, G.S. McCaleb and J.A. Montgomery, J. Med. Chem., 18, 104 (1975); T. Anderson, M.G. McMenamin and P.S. Schein, Cancer Res., 35, 761 1975).
7. B. Serrou, P.S. Schein and J.L. Imbach, Eds., Nitrosoureas in Cancer Treatment, Inserm Symposium No 19, pp 249. Elsevier, Amsterdam 1981; B. Bannister, J. Antibiot., 25, 377 (1972) ; P.S. Schein, M.G. McMenamin and T. Anderson, Cancer Res., 33, 2005 (1973); J.J. Vavra, C. DeBoer, A. Dietz, L.J. Hanka and W.T. Sokolski, Antibiot. Ann. 1959/1960, 230, R.R. Herr, H.K. Jahnke and A.D. Argoudelis, J. Am. Chem. Soc., 89, 4808 (1967); E.J. Hessler and H.K. Jahnke, J. Org. Chem., 35, 245 (1970); T.P. Johnston, G.S. McCaleb and J.A. Montgomery, J. Med. Chem., 18, 104 (1975); T. Anderson, M.G. McMenamin and P.S. Schein, Cancer Res., 35, 761 1975).
8. B. Serrou, P.S. Schein and J.L. Imbach, Eds., Nitrosoureas in Cancer Treatment, Inserm Symposium No 19, pp 249. Elsevier, Amsterdam 1981; B. Bannister, J. Antibiot., 25, 377 (1972) ; P.S. Schein, M.G. McMenamin and T. Anderson, Cancer Res., 33, 2005 (1973); J.J. Vavra, C. DeBoer, A. Dietz, L.J. Hanka and W.T. Sokolski, Antibiot. Ann. 1959/1960, 230, R.R. Herr, H.K. Jahnke and A.D. Argoudelis, J. Am. Chem. Soc., 89, 4808 (1967); E.J. Hessler and H.K. Jahnke, J. Org. Chem., 35, 245 (1970); T.P. Johnston, G.S. McCaleb and J.A. Montgomery, J. Med. Chem., 18, 104 (1975); T. Anderson, M.G. McMenamin and P.S. Schein, Cancer Res., 35, 761 1975).
9. B. Piekarska-Bartoszewicz and A. Temeriusz, J. Carbohydr. Chem., 12, 913 (1993).
10. I. Wawer. B. Piekarska-Bartoszewicz and A. Temeriusz, Carbohydr. Res., 279, 83 (1995).
11. R. Anulewicz, I. Wawer, B. Piekarska-Bartoszewicz and A. Temeriusz, Carbohydr. Res., 281, 1 (1996). *
12. G.M Sheldrick, (1993), SHELXL93, Program for the Refinement of Crystal Structures. University of Göttingen, Germany.
13. D. Cremer and J.A. Pople, J. Am. Chem. Soc., 97, 1354 (1975).
14. J.D. Oliver and L.C. Strickland, Acta Crystallogr., Sect. B. 40, 820 (1984).
15. M. Plass, A. Kolbe, I. Wawer, B. Piekarska-Bartoszewicz and A. Temeriusz, J. Phys. Org. Chem. (in press).
16. G.M. Sheldrick, Acta Crystallogr., Sect. A, 46 467(1990).
17. International Tables for X-ray Crystallography, 1974, Vol. IV, Birmigham, Kynoch (present distributor, Kluver Academic Publishers, Dordrecht ).
18. Tables of atomic coordinates, bond lengths, and bond angles have been deposited with the Cambridge Crystallographic Data Centre. These tables may be obtained, on request, from the Director, Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2 1EZ UK. * By computer mistake incorrect structure is given in the ref. 4; figures 1, 2, and 3 of the cited paper showed the mirror images of methyl 3,4,6-tri-O-acetyl-2-deoxy-2-[3-(2-phenylethyl)-ureido]-β-D- glucopyranoside. Correct molecular structure of methyl 3,4,6-tri-O-acetyl-2-deoxy-2-[3-(2-phenyl-ethyl)-ureido]-β-D- glucopyranoside.