The potential of N-alkoxymethyl groups as peptide backbone protectants

Tetrahedron Letters

Volumn 55, Issue 1, 2014, Pages 184-188

  Fernández Llamazares, Ana I ^a,b   Spengler, Jan ^a,b   Albericio, Fernando ^a,b,c,d  

^a INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

^b BIOMATERIALES Y NANOMEDICINA CIBER BBN   (Spain)

^c UNIVERSITY OF BARCELONA   (Spain)

^d UNIVERSITY OF KWAZULU NATAL   (South Africa)

Author keywords

Backbone N alkylation; Backbone protecting groups; N Alkoxymethyl; Peptides; SPPS

Indexed keywords

METHYL GROUP; N ALKOXYMETHYL GROUP; PEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ALKYLATION; AMINO ACID SEQUENCE; ARTICLE; CHEMICAL STRUCTURE; DEPROTECTION REACTION; NUCLEOPHILICITY; OXIDATION; PEPTIDE SYNTHESIS; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID PHASE SYNTHESIS; SUBSTITUTION REACTION;

EID: 84890145789     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.10.149     Document Type: Article

References (19)

1. C. Hyde, T. Johnson, D. Owen, M. Quibell, and R.C. Sheppard Int. J. Pept. Protein Res. 43 1994 431 440
2. T. Johnson, M. Quibell, D. Owen, and R.C. Sheppard J. Chem. Soc., Chem. Commun. 1993 369 372
3. T. Johnson, L.C. Packman, C.B. Hyde, D. Owen, and M. Quibell J. Chem. Soc., Perkin Trans. 1 1996 719 728
4. L.A. Carpino, D. Nasr, A.A. Abdel-Maksoud, A. El-Faham, D. Ionescu, P. Henklein, H. Wenschuh, M. Beyermann, E. Krause, and M. Bienert Org. Lett. 11 2009 3718 3721
5. A. Isidro-Llobet, X. Just-Baringo, M. Álvarez, and F. Albericio Biopolymers 90 2008 444 449
6. T. Haack, and M. Mutter Tetrahedron Lett. 33 1992 1589 1592
7. M. Mutter, A. Nefzi, T. Sato, X. Sun, F. Wahl, and T. Wuhr Pept. Res. 8 1995 145 153
8. T. Wöhr, F. Wahl, A. Nefzi, B. Rohwedder, T. Sato, X. Sun, and M. Mutter J. Am. Chem. Soc. 118 1996 9218 9227
9. M. Goodman, A. Felix, L. Moroder, and C. Toniolo Houben-Weyl Methods in Organic Chemistry E22 Synthesis of Peptides and Peptidomimetics Vol. 1 (E22a) 2002-2003 Thieme: Stuttgart New York 338 339 Chapter 2
10. P.J. Kocienski Protecting Groups 2000 Georg Thieme Verlag: Stuttgart New York 561 565 Chapter 8
11. Bartl, R.; Frank, R. International patent WO 92/22566, 1992.
12. H. Sun, C. Martin, D. Kesselring, R. Keller, and K.D. Moeller J. Am. Chem. Soc. 128 2008 13761 13771
13. J. Spengler, and K. Burger Synthesis 1998 67 70
14. J. Spengler, and K. Burger J. Chem. Soc., Perkin Trans. 1 1998 2091 2093
15. H. Schedel, and K. Burger Monatsh. Chem. 131 2000 1011 1018
16. L. Kocsis, T. Bruckdorfer, and G. Orosz Tetrahedron Lett. 49 2008 7015 7017
17. F. Falb, T. Yechezkel, Y. Salitra, and C. Gilon J. Pept. Res. 53 1999 507 517
18. B. Thern, J. Rudolph, and G. Jung Tetrahedron Lett. 43 2002 5013 5016
19. M.A. Mitchell, T.A. Runge, W.R. Mathews, A.K. Ichhpurani, N.K. Harn, P.J. Dobrowolski, and F.M. Eckenrode Int. J. Protein Res. 36 1990 350 355