Solid phase synthesis of oligoureas using O-succinimidyl-(9H-fluoren-9- ylmethoxycarbonylamino)ethylcarbamate derivatives as activated monomers

Tetrahedron Letters

Volumn 41, Issue 10, 2000, Pages 1553-1557

  Guichard, Gilles ^a   Semetey, Vincent ^a   Rodriguez, Marc ^b   Briand, Jean Paul ^a  

^a INSTITUT DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

^b Neosystem   (France)

Author keywords

Carbamates; Oligomers; Solid phase synthesis; Ureas

Indexed keywords

MONOMER; UREA DERIVATIVE; URETHAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034603443     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02353-9     Document Type: Article

References (20)

1. Liskamp, R. M. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 633-636.
2. Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015-2022.
3. Soth, M. J.; Nowick, J. S. Curr. Opin. Chem. Biol. 1997, 1, 120-129.
4. Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180.
5. Guichard, G. In Solid Phase Synthesis: A Practical Guide; Kates, S.; Albericio, F., Eds. Solid phase synthesis of pseudopeptides and oligomeric peptide backbone mimetics. Marcel Dekker: New York, in press.
6. (a) Burgess, K.; Linthicum, D. S.; Shin, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 907-908.
7. (b) Burgess, K.; Ibarzo, J.; Linthicum, D. S.; Russell, D. H.; Shin, H.; Shitangkoon, A.; Totani, R.; Zhang, A. J. J. Am. Chem. Soc. 1997, 119, 1556-1564.
8. Nowick, J. S. Acc. Chem. Res. 1999, 32, 287-296.
9. Tamilarasu, N.; Huq, I.; Rana, T. M. J. Am. Chem. Soc. 1999, 121, 1597-1598.
10. Kim, J. M.; Bi, Y.; Paikoff, S. J.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5305-5308.
11. Boeijen, A.; Liskamp, R. M. J. Eur. J. Org. Chem. 1999, 2127-2135.
12. Guichard, G.; Semetey, V.; Didierjean, C.; Aubry, A.; Briand, J. P.; Rodriguez, M. J. Org. Chem. 1999, 64, 8702-8705.
13. 3-HXaa-OH) 1 were prepared as previously described: Guichard, G.; Abele, S; Seebach, D. Helv Chim. Acta 1998, 81, 187-206.
14. 12
15. +.
16. +.
17. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970, 34, 595-598.
18. 3-HXaa identifies the β-amino acid from which carbamate 4 is derived.
19. Rink, H. Tetrahedron Lett. 1987, 28, 3787-3790.
20. Anchoring of the first monomer to the resin was monitored with ninhydrin test. However, as the chain was growing, the trinitrobenzenesulfonic acid test was found to be more reliable.