A facile synthesis of C-terminal neoglycopeptides: Incorporation of urea moiety between sugars and peptides employing curtius rearrangement

International Journal of Peptide Research and Therapeutics

Volumn 14, Issue 1, 2008, Pages 34-40

  Sureshbabu, Vommina V ^a   Venkataramanarao, Rao ^a   Hemantha, H P ^a  

^a BANGALORE UNIVERSITY   (India)

Author keywords

Curtius rearrangement; Fmoc peptidyl isocyanates; Glycosylamine; Neoglycopeptides; Ureido group

Indexed keywords

AMINOSUGAR; CARBAMIC ACID DERIVATIVE; GLYCOPEPTIDE; ISOCYANIC ACID DERIVATIVE; PEPTIDE; PEPTIDE DERIVATIVE; SUGAR; UREA;

ARTICLE; CARBOXY TERMINAL SEQUENCE; CURTIUS REARRANGEMENT; DRUG SYNTHESIS; MASS SPECTROMETRY; MOLECULAR STABILITY; PEPTIDE SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE;

EID: 40049087671     PISSN: 15733149     EISSN: 15733904     Source Type: Journal    
DOI: 10.1007/s10989-007-9101-4     Document Type: Article

References (17)

1. Avalos, M., Bubiano, R., Cintas, P., Palacios, J. C., and Perol, E. H. S.: 2006, Eur. J. Org. Chem. 657-671
2. Castro, J. L., Ball, R. G., Broughton, H. B., Russel, M. G. N., Rathbone, D. D., Watt, A. P., Baker, R., Chapman, K. L., Fletcher, A. E., Patel, S., Smith, A. J., Marshal, G. R., Ryecroft, W., Matassa, V. J.: 1996, J. Med. Chem. 39, 842-849
3. Bottcher, C., Burger, K.: 2003, Tetrahedron Lett. 44, 4223-4226
4. Deng, S., Gangadharmath, U., Chang, C. T.: 2006, J. Org. Chem. 71, 5179-5185
5. Furniss, B. S., Hannaford, A. J., Smith, P. W. G., and Tatchell, A. R.: 1989, Vogel's Textbook of Practical Organic Chemistry, 5th edition, Addison Wesley Longman Limited.
6. Boons, G-J.: 1998, Carbohydrate Chemistry, University of Birmingham. U.K. lakie Academic and Professional, Thomson Publishing.
7. Ichikawa, Y., Ohara, F., Kotsuki, H., Nakano, K.: 2006, Org. Lett. 8, 5009-5012
8. Katritzky, A. R., Angrish, P., Suzuki, K.: 2006, Synthesis 3, 411-424
9. Kihlberg, J., Ahman, J., Walse, B., Drakenberg, T., Nilsson, A., Soderberg-Ahlm, C., Bengtsson, B., Olsson, H.: 1995, J. Med. Chem. 38, 161-169
10. Kunz, H.: 1987, Angew. Chem. Int. Ed. Engl. 26, 294-308
11. Maya, I., Lopez, O., Maza, S.: 2003, Tetrahedron Lett. 44, 8539-8543
12. Patil, B. S., Vasanthakumar, G. R., Suresh Babu, V. V.: 2003, J. Org. Chem. 68, 7274-7278
13. Salvador, L. A., Elofsson, M., Kihlberg, J.: 1995, Tetrahedron 51, 5643-5656
14. Spengler, J., Bottcher, C., Albericio, F., Burger, K.: 2006, Chem. Rev. 106, 4728-4746
15. Sureshbabu, V. V., Patil, B. S., Venkataramanarao, R.: 2006, J. Org. Chem. 71, 7697-7705.
16. Tantry, S. J., Suresh Babu V. V.: 2002, Lett. Pept. Sci. 9, 35-41
17. Taylor, C. M.: 1998, Tetrahedron 54, 11317-11362