1-(t-butyldimethylsilyloxy) benzotriazole (TBDMS-OBt): A new and novel reagent for the synthesis of peptides

Letters in Peptide Science

Volumn 9, Issue 1, 2002, Pages 35-41

  Tantry, Subramanyam J ^a   Suresh Babu, Vommina V ^a  

^a BANGALORE UNIVERSITY   (India)

Author keywords

Dialkyl amino acids; N methyl amino acids; Racemization free coupling; TBDMS OBt

Indexed keywords

1 (TERT BUTYLDIMETHYLSILYLOXY)BENZOTRIAZOLE; AMINO ACID DERIVATIVE; ESTER; PEPTIDE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; PEPTIDE SYNTHESIS; PROTEIN ISOLATION; PROTEIN PURIFICATION; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0036946496     PISSN: 09295666     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1021307501833     Document Type: Article

References (23)

1. Lott, R. S., Chauhan, V. S. and Stammer, C. H., J. Chem. Soc. Chem. Commun., (1979) 495.
2. Kaiser Sr., E., Kubaik, T. M., Tam, J. P. and Merrifield, R. B., Tetrahedron Lett., 29 (1998) 303.
3. Sivanandaiah, K. M., Suresh Babu, V. V. and Shankaramma, S. C., Int. J. Pept. Prot. Res., 45 (1995) 377.
4. Mattem, R. H., Gunasekara, S. P. and Mcconnel, O. J., Tetrahedron Lett., 38 (1997) 2197.
5. Corey, E. J. and Venkateshwarlu, A., J. Am. Chem. Soc., 94 (1972) 69.
6. Corey, E. J. and Venkateshwarlu, A., J. Am. Chem. Soc., 94 (1992) 6190.
7. Carpino, L. A., Cohen, B. J., Kenton, E., Stephen Jr., S., Sadat-Aalee, S. Y. Tien, J.-H. and Lengridge, D. C., J. Org. Chem., 51 (1986) 3732.
8. Carpino, L. A., Beyermann, M., Wensehuh, H. and Bienert, M., Acc. Chem. Res., 29 (1996) 268.
9. Albercio, F., Chinchilla, R., Dodsworth, D. J. and Najera, C., Org. Prep. Proc. Int., 33 (2001) 203.
10. Carpino, L. A., Chao, H.-G., Beyermann, M. and Bienert, M., J. Org. Chem., 56 (1991) 2635.
11. Sivanandaiah, K. M., Suresh Babu, V. V. and Shankaramma, S. C., Int. J. Peptide Protein Res., 44 (1994) 24.
12. Suresh Babu, V. V. and Gopi, H. N., Tetrahedron Lett., 39 (1998) 1049.
13. Gopi, H. N. and Suresh Babu, V. V., Ind. J. Chem., 37B (1998) 394.
14. Gopi, H. N. and Suresh Babu, V. V., Tetrahedron Lett., 39 (1998) 9769.
15. Suresh Babu, V. V. and Ananda, K., Lett. Pept. Sci., 7 (2000) 41.
16. Carpino, L. A., Ionescu, D., El-Faham, A., Wenschuh, H., Bienert, M. and Beyermann, M., Tetrahedron Lett., 39 (1998) 241.
17. Brunissen, A., Ayoub, M. and Laviella, S., Tetrahedron Lett., 37 (1996) 6713.
18. Leggio,ed A., Liguori, A., Procopio, A. and Sindona, G., J. Chem. Soc. Perkin Trans., 1 (1997) 1969.
19. Suresh Babu, V. V., Ananda, K. and Vasanthakumar, G.-R., J. Chem. Soc. Perkin Trans., 1 (2000) 4328.
20. Carpino, L. A., J. Org. Chem., 53 (1988) 875.
21. Ananda, K. and Suresh Babu, V. V., J. Pept. Res., 57 (2001) 223.
22. Albericio, F., Bofill, J. M., El-Faham, A. and Kates, S. A., J. Org. Chem., 63 (1998) 9678.
23. Recently 1-(trimethylsilylmethyl) benzotriazole was used in homologation of carboxylic acids as a safe alternative to the Amdt-Eistert reaction by Katritzky, R., Zhang, S., Hussein, A. H. M. and Fang, Y., J. Org. Chem., 66 (2001) 5606.