Stereospecific synthesis and characterization of aminoglycoside ligands from diethylenetriamine

Journal of Organic Chemistry

Volumn 64, Issue 11, 1999, Pages 4012-4015

  Gaucher, Sara P ^a   Pedersen, Steven F ^a   Leary, Julie A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOGLYCOSIDE ANTIBIOTIC AGENT; DIETHYLENETRIAMINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTALLIZATION; DIASTEREOISOMER; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOSPECIFICITY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033612386     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9900331     Document Type: Article

References (25)

1. Chaplin, M. F., Kennedy, J. F., Eds. Carbohydrate Analysis; Oxford: New York, 1994.
2. Fukuda, M., Kobata, A., Eds. Glycobiology; Oxford: New York, 1993.
3. Asam, M. R.; Glish, G. L. J. Am. Soc. Mass Spectrom. 1998, 8, 987.
4. Weiskopf, A. S.; Vouros, P.; Harvey, D. J. Rapid Commun. Mass Spec. 1997, 11, 1493.
5. Hofmeister, G. E.; Zhou, Z.; Leary, J. A. J. Am. Chem. Soc. 1991, 113, 5964.
6. Zhou, Z.; Ogden, S.; Leary, J. A. J. Org. Chem. 1990, 55, 5444.
7. Fura, A.; Leary, J. A. Anal. Chem. 1993, 65, 2805.
8. Staempfli, A.; Zhou, Z.; Leary, J. A. J. Org. Chem. 1994, 59, 3590.
9. Gaucher, S. P.; Leary, J. A. Anal. Chem. 1998, 70, 3009.
10. Smith, G.; Leary, J. A. J. Am. Soc. Mass Spectrom. 1996, 7, 953.
11. Gaucher, S. P.; Leary, J. A. J. Am. Soc. Mass Spectrom. 1999, 10, 269.
12. Smith, G.; Leary, J. A. J. Am. Chem. Soc. 1996, 118, 3293.
13. Smith, G.; Pedersen, S. F.; Leary, J. A. J. Org. Chem. 1997, 62, 2152.
14. Smith, G.; Leary, J. A. J. Am. Chem. Soc. 1998, 120, 13046.
15. Lammers, H.; Peters, J. A.; vanBekkum, H. Tetrahedron 1994, 59, 8103.
16. MacLeod, J. M. Carbohydr. Res. 1979, 75, 71.
17. Mitts, E.; Hixon, R. M. J. Am. Chem. Soc. 1944, 66, 483.
18. Ledl, F.; Schleicher, E. Angew. Chem., Int. Ed. Engl. 1990, 29, 565.
19. Amadori, M. Atti R. Accad. Naz. Lincei Mem. Cl. Sci. Fis. Mater. Nat. 1931, 13, 72.
20. Micheel, F.; Frowein, A. Chem. Ber. 1967, 90, 1599.
21. Micheel, F.; Hagemann, G. Chem. Ber. 1959, 92, 2836.
22. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds, 5th ed.; John Wiley: New York, 1991; p 221.
23. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry Part A, 3rd ed.; Plenum: New York, 1990; pp 147-150.
24. Yano, S. Coord. Chem. Rev. 1988, 92, 113.
25. Yano, S.; Kato, M.; Shioi, H.; Takahashi, T.; Tsubomura, T.; Toriumi, K.; Ito, T.; Hidai, M.; Yoshikawa, S. J. Chem. Soc., Dalton Trans. 1993, 1699.