Polymer-bound TBTU as a new solid-supported reagent for peptide synthesis

Tetrahedron Letters

Volumn 41, Issue 14, 2000, Pages 2463-2466

  Chinchilla, Rafael ^a   Dodsworth, David J ^a   Naájera, Carmen ^a   Soriano, Joseé M ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Aminium salts; Coupling reagents; Peptides; Polymers

Indexed keywords

BENZOTRIAZOLE DERIVATIVE; POLYMER; POLYSTYRENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; FILTRATION; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; REACTION ANALYSIS;

EID: 0034175691     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00180-5     Document Type: Article

References (27)

1. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554. (b) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678. (c) Brown, R. Contemp. Org. Synth. 1997, 216-237. (d) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42. (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett. 1998, 817-827. (h) Wenworth Jr., R.; Janda, K. D. Chem. Commun. 1999, 1917-1924. (i) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (j) James, I. W. Tetrahedron 1999, 55, 4855-4946.
2. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554. (b) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678. (c) Brown, R. Contemp. Org. Synth. 1997, 216-237. (d) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42. (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett. 1998, 817-827. (h) Wenworth Jr., R.; Janda, K. D. Chem. Commun. 1999, 1917-1924. (i) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (j) James, I. W. Tetrahedron 1999, 55, 4855-4946.
3. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554. (b) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678. (c) Brown, R. Contemp. Org. Synth. 1997, 216-237. (d) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42. (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett. 1998, 817-827. (h) Wenworth Jr., R.; Janda, K. D. Chem. Commun. 1999, 1917-1924. (i) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (j) James, I. W. Tetrahedron 1999, 55, 4855-4946.
4. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554. (b) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678. (c) Brown, R. Contemp. Org. Synth. 1997, 216-237. (d) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42. (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett. 1998, 817-827. (h) Wenworth Jr., R.; Janda, K. D. Chem. Commun. 1999, 1917-1924. (i) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (j) James, I. W. Tetrahedron 1999, 55, 4855-4946.
5. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554. (b) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678. (c) Brown, R. Contemp. Org. Synth. 1997, 216-237. (d) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42. (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett. 1998, 817-827. (h) Wenworth Jr., R.; Janda, K. D. Chem. Commun. 1999, 1917-1924. (i) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (j) James, I. W. Tetrahedron 1999, 55, 4855-4946.
6. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554. (b) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678. (c) Brown, R. Contemp. Org. Synth. 1997, 216-237. (d) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42. (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett. 1998, 817-827. (h) Wenworth Jr., R.; Janda, K. D. Chem. Commun. 1999, 1917-1924. (i) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (j) James, I. W. Tetrahedron 1999, 55, 4855-4946.
7. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554. (b) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678. (c) Brown, R. Contemp. Org. Synth. 1997, 216-237. (d) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42. (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett. 1998, 817-827. (h) Wenworth Jr., R.; Janda, K. D. Chem. Commun. 1999, 1917-1924. (i) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (j) James, I. W. Tetrahedron 1999, 55, 4855-4946.
8. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554. (b) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678. (c) Brown, R. Contemp. Org. Synth. 1997, 216-237. (d) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42. (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett. 1998, 817-827. (h) Wenworth Jr., R.; Janda, K. D. Chem. Commun. 1999, 1917-1924. (i) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (j) James, I. W. Tetrahedron 1999, 55, 4855-4946.
9. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554. (b) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678. (c) Brown, R. Contemp. Org. Synth. 1997, 216-237. (d) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42. (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett. 1998, 817-827. (h) Wenworth Jr., R.; Janda, K. D. Chem. Commun. 1999, 1917-1924. (i) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (j) James, I. W. Tetrahedron 1999, 55, 4855-4946.
10. For recent reviews on polymer-supported chemistry, see: (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527-4554. (b) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678. (c) Brown, R. Contemp. Org. Synth. 1997, 216-237. (d) Früchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17-42. (e) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489-509. (f) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320. (g) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett. 1998, 817-827. (h) Wenworth Jr., R.; Janda, K. D. Chem. Commun. 1999, 1917-1924. (i) Lorsbach, B. A.; Kurth, M. J. Chem. Rev. 1999, 99, 1549-1581. (j) James, I. W. Tetrahedron 1999, 55, 4855-4946.
11. Desai, M. C.; Stephens Stramiello, L. M. Tetrahedron Lett. 1993, 34, 7685-7688.
12. Pop, I. E.; Déprez, B. P.; Tartar, A. L. J. Org. Chem. 1997, 62, 2594-2603.
13. (a) Dendrinos, K. G.; Jeong, J.; Huang, W.; Kalivretenos, A. G. Chem. Commun. 1998, 499-500.
14. (b) Huang, W.; Kalivretenos, A. G. Tetrahedron Lett. 1995, 36, 9113-9116.
15. Polymer 3 has also been used for the synthesis of N-hydroxysuccinimide esters: (a) Dendrinos, K. G.; Kalivretenos, A. G. Tetrahedron Lett. 1998, 39, 1321-1324; and for the protection of amides as carbamates with the Cbz, Fmoc and Boc groups: (b) Dendrinos, K. G.; Kalivretenos, A. G. J. Chem. Soc., Perkin Trans 1 1998, 1463-1464.
16. Polymer 3 has also been used for the synthesis of N-hydroxysuccinimide esters: (a) Dendrinos, K. G.; Kalivretenos, A. G. Tetrahedron Lett. 1998, 39, 1321-1324; and for the protection of amides as carbamates with the Cbz, Fmoc and Boc groups: (b) Dendrinos, K. G.; Kalivretenos, A. G. J. Chem. Soc., Perkin Trans 1 1998, 1463-1464.
17. Kalir, R.; Warshawsky, A.; Fridkin, M.; Patchornik, A. Eur. J. Biochem. 1975, 59, 55-61.
18. Mokotoff, M.; Zhao, M.; Roth, S. M.; Shelley, J. A.; Slavoski, J. N. Kouttab, N. M. J. Med. Chem. 1990, 33, 354-360.
19. König, W.; Geiger, R. Chem. Ber. 1970, 103, 788-798.
20. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397-4398.
21. Bailén, M. A.; Chinchilla, R.; Dodsworth, D. J.; Nájera, C. J. Org. Chem. 1999, 64, 8936-8939.
22. The same strong band was observed in a IR spectrum of TBTU.
23. Abdelmoty, I.; Albericio, F.; Carpino, L. A.; Foxman, B. M.; Kates, S. A. Lett. Pept. Sci. 1994, 1, 57-67.
24. Van der Auwera, C.; Van Damme, S.; Anteunis, M. J. O. Int. J. Pept. Protein. Res. 1987, 29, 464-471.
25. Williams, M. W.; Young, G. T. J. Chem. Soc. 1963, 881-889.
26. TBTU: Anteunis' test, 1.1% D-isomer. Young's test, 39% D-isomer (Knorr, R.; Trzeciak, A.; Bannwarth, W.; Gillessen, D. Tetrahedron Lett. 1989, 30, 1927-1930). HATU: Anteunis' test, no epimerization. Young's test, 20% D-isomer (Ref. 10).
27. 4) and the solvent was evaporated (15 torr) affording the corresponding peptide.