Solid-phase synthesis with tris(alkoxy)benzyl backbone amide linkage (BAL)

Chemistry - A European Journal

Volumn 5, Issue 10, 1999, Pages 2787-2795

  Alsina, Jordi ^a,b   Jensen, Knud J ^a,c   Albericio, Fernando ^a,b   Barany, George ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b UNIVERSITY OF BARCELONA   (Spain)

^c TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

Carbohydrates; Combinatorial chemistry; Handles; Libraries; Linkers; Peptides; Solid phase synthesis

Indexed keywords

AMIDE; OLIGONUCLEOTIDE; ORGANIC COMPOUND; PEPTIDE; PROTEIN;

AMINATION; CHEMICAL BOND; DECOMPOSITION; PEPTIDE SYNTHESIS; REACTION ANALYSIS; REDUCTION; REVIEW; SOLID STATE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0032823018     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19991001)5:10<2787::AID-CHEM2787>3.0.CO;2-2     Document Type: Short Survey

References (57)

1. a) R. B. Merrifield, J. Am. Chem. Soc. 1963, 85, 2149-2154;
2. b) R. B. Merrifield, Science 1986, 232, 341-347.
3. a) G. Barany, R. B. Merrifield, in The Peptides, Vol. 2 (Eds.: E. Gross, J. Meienhofer), Academic Press, New York, 1979, pp. 1-284;
4. b) E. Atherton, R. C. Sheppard, Solid Phase Peptide Synthesis: A Practical Approach; IRL, Oxford (UK), 1989;
5. c) G. B. Fields, Z. Tian, G Barany, in Synthetic Peptides: A User's Guide (Ed.: G. A Grant), W. H. Freeman, New York, 1992; pp. 259-345;
6. d) P. Lloyd-Williams, F. Albericio, E. Giralt, Chemical Approaches to the Synthesis of Peptides and Proteins, CRC, Boca Raton, 1997.
7. a) Oligonucleotide Synthesis, A Practical Approach (Ed.: M. J. Gait), IRL, Oxford (UK), 1984;
8. b) S. L. Beaucage, R. P. Iyer, Tetrahedron 1992, 48, 2223-2311.
9. a) K. S. Lam, M. Lebl, V. Krchnák, Chem. Rev. 1997, 97, 411-448;
10. b) A. Nefzi, J. M Ostresh, R. A. Houghten, Chem. Rev. 1997, 97, 449-472;
11. c) A Practical Guide to Combinatorial Chemistry (Eds.: A. W. Czarnik, S. H. DeWitt), American Chemical Society, Washington, DC, 1997;
12. d) Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular Weight Compound Libraries, (Eds.: D. Obrecht, J. M. Villalgordo), Pergamon, Oxford (UK), 1998.
13. M. F. Songster, G. Barany, Methods Enzymol. 1997, 289, 126-174.
14. a) K. J. Jensen, M. F. Songster, J. Vágner, J. Alsina, F. Albericio, G. Barany, in Peptides-Chemistry, Structure and Biology: Proceedings of the Fourteenth American Peptide Symposium (Eds.: P. T. P. Kaumaya, R. S. Hodges), Mayflower Scientific, Kingswinford (UK), 1996; pp. 30-32;
15. b) K. J. Jensen, M. F. Songster, J. Vágner, J. Alsina, F. Albericio, G. Barany, in Innovation and Perspectives in Solid Phase Synthesis and Combinatorial Chemical Libraries, 1996, Collected Papers, Fourth International Symposium (Ed.: R. Epton), Mayflower Scientific, Kingswinford (UK) 1996, pp. 187-190.
16. K. J. Jensen, J. Alsina, M. F. Songster, J. Vágner, F. Albericio, G. Barany, J. Am. Chem. Soc. 1998, 120, 5441-5452.
17. a) F. Albericio, U. Slomczynska, G. Barany, in Forum Peptides: Proceedings of the 1st International Forum Peptides, (Eds.: B. Castro; J. Martínez), Les Impressions Dohr, Nancy (France), 1986, pp. 1-5;
18. b) F. Albericio; G. Barany, Int. J. Peptide Protein Res. 1987, 30, 206-216;
19. c) F. Albericio, N. Kneib-Cordonier, S. Biancalana, L. Gera, R. I. Masada, D. Hudson, G. Barany, J. Org. Chem. 1990, 55, 3730-3743.
20. For all structural formulas in this review, PALdehyde and BAL handles are depicted as the isomer in which the aminomethyl moiety is para to the valeryl linking group. Some experiments described herein started instead with a mixture (1:2) of the ortho and para isomers of PALdehyde, that is, o,p-PALdehyde; furthermore, the side-chain moiety had one fewer carbon (substitution of butyryl for valeryl). The latter compound is commercially available from PerSeptive Biosystems (Framingham, MA). We have previously shown that the length of the aliphatic spacer separating the electron-donating oxygen from the carboxamide link to the resin affects the lability of the resultant handle to acid. Compounds with three and four methylenes in the side chain were more labile that those with a single methylene. See F. Albericio; G. Barany, Int. J. Peptide Protein Res. 1985, 26, 92-97, and refs. [8a,b].
21. An alternative synthesis of 4-hydroxy-2,6-dimethoxybenzaldehyde was reported by J. J. Landi, K. Ramig, Synth. Comm. 1991, 21, 167-171.
22. S. K. Sharma, M. F. Songster, T. L. Colpitts, P. Hegyes, G. Barany, F. J. Castellino, J. Org. Chem. 1993, 58, 4993-4996.
23. M. F. Songster, J. Vágner, G. Barany, Lett. Pept. Sci. 1996, 2, 265-270.
24. F. Albericio, G. Barany. Tetrahedron Lett. 1991, 32, 1015-1018.
25. a) F. Weygand, W. Steglich, J. Bjarnason, Tetrahedron Lett. 1966, 3483-3487;
26. b) M. Narita, T. Fukunaga, A. Wakabayashi, K. Ishikawa, H. Nakano, Int. J. Pept. Protein Res. 1984, 23, 306-314;
27. c) J. Blaakmeer, T. Tijsse-Klasen, G. I. Tesser, Int. J. Pept. Protein Res. 1991, 37, 556-564;
28. d) T. Johnson, M. Quibell, R. C. Sheppard, J. Pept. Sci. 1995, 1, 11-25;
29. e) M. Quibell, L. C. Packman, T. Johnson, J. Am. Chem. Soc. 1995, 117, 11656-11668;
30. f) R. G. Simmonds, Int. J. Pept. Protein Res. 1996, 47, 36-41;
31. g) T. Johnson, L. C. Packman, C. B. Hyde, D. Owen, M. Quibell, J. Chem. Soc. Perkin Trans. 1 1996, 719-728;
32. h) E. Nicolás, M. Pujades, J. Bacardit, E. Giralt, F. Albericio, Tetrahedron Lett. 1997, 38, 2317-2320.
33. Similar results were obtained using as solvent HOAc/MeOH (1:100), MeOH/THF (1:4) or allyl alcohol. Reaction was incomplete in iPrOH, while in DMF (neat) or HOAc/DMF (1:100) the desired secondary amines (4) were sometimes minor whereas the major products were the di-BAL-kylated tertiary amines, apparently formed by addition of a second equivalent of 1.
34. a) G. Barany, F. Albericio, N. A. Solé, G. W. Griffin, S. A. Kates, D. Hudson, in Peptides 1992: Proceedings of the Twenty-Second European Peptide Symposium (Eds.: C. H. Schneider, A. N. Eberle), ESCOM Science, Leiden (The Netherlands) 1993, pp. 267-268;
35. b) S. Zalipsky, J. L. Chang, F. Albericio, G. Barany, React. Polym. 1994, 22, 243-258;
36. c) G. Barany, F. Albericio, S. A. Kates, M. Kempe, in Chemistry and Biological Application of Polyethylene Glycol, ACS Symposium Series 680 (Eds.: J. M. Harris, S. Zalipsky) American Chemical Society Books, Washington, DC, 1997, pp. 239-264.
37. Y. Sasaki, D. H. Coy, Peptides 1987, 8, 119-121.
38. Solvents of choice were DMF, as reported by Sasaki and Coy in ref. [17], or MeOH as suggested by solution precedents (this work, covered previously). Given the tendency for dialkylation in solution with DMF as solvent (see ref. [15]), the relative absence of such an unfavorable side reaction in the solid-phase case is taken as evidence for relative site isolation, as has been covered in numerous review articles. The success of on-resin mono-reductive amination in DMF is also attributable to the considerable excess of amine, later removed readily by filtration and washing, that can be used in the reaction. In the solution case, use of excess amine leads to complications in the workup and purification of the Fmoc-protected preformed handle 3.
39. J. Alsina, E. Giralt, F. Albericio, Tetrahedron Lett. 1996, 37, 4195-4198.
40. a) M. del Fresno, J. Alsina, M. Royo, G. Barany, F. Albericio, Tetrahedron Lett. 1998, 39, 2639-2642;
41. b) F. Albericio, M. del. Fresno, A. Frieden, M. Royo, J. Alsina, K. J. Jensen, S. A. Kates, G. Barany, in Peptides-Chemistry, Structure and Biology: Proceedings of the Fifteenth American Peptide Symposium (Eds.: J. P. Tam, P. T. P. Kaumaya), Kluwer, Dordrecht (The Netherlands), 1999, pp. 37-39;
42. c) F. Albericio, A. Frieden, M. del Fresno, M. Royo, J. Alsina, K. J. Jensen, S. A. Kates, G. Barany, in Innovation and Perspectives in Solid Phase Synthesis and Combinatorial Chemical Libraries, 1998, Collected Papers, Fifth International Symposium; (Ed.: R. Epton), Mayflower Scientific, Birmingham (UK), 1999, pp. 7-10;
43. d) M. Royo, M. del Fresno, A. Frieden, W. Van den Nest, M. Sanseverino, J. Alsina, S. A. Kates, G. Barany, F. Albericio, React. Funct. Polym. 1999, 41, 103-110.
44. a) C. G. Boojamra, K. M. Burow, J. A. Ellman, J. Org. Chem. 1995, 60, 5742-5743;
45. b) C. G. Boojamra, K. M. Burow, L. A. Thompson, J. A. Ellman, J. Org. Chem. 1997, 62, 1240-1256.
46. N. S. Gray, S. Kwon, P. G. Schultz, Tetrahedron Lett. 1997, 38, 1161-1164.
47. K. Ngu, D. V. Patel, J. Org. Chem. 1997, 62, 7088-7089.
48. C. T. Bui, F. A. Rasoul, F. Ercole, Y. Pham, N. J. Maeji, Tetrahedron Lett. 1998, 39, 9279-9282.
49. J. Alsina, T. S. Yokum, F. Albericio, G. Barany, in Peptides for the New Millenium: Proceedings of the 16th American Peptide Symposium (Eds.: G. B. Fields, J. P. Tam, G. Barany), Kluwer Academic, Dordrecht (The Netherlands), in press.
50. J. F. Tolborg, K. J. Jensen, Poster BP 288, XIXth International Carbohydrate Symposium, San Diego, August 9-14, 1998.
51. Bis(alkoxy)benzyl amide versions of BAL have beeen reported: a) E. E. Swayze, Tetrahedron Lett. 1997, 38, 8465-8468;
52. b) A. M. Fivush, T. M. Wilson, Tetrahedron Lett. 1997, 38, 7151-7154;
53. c) D. Sarantakis, J. J. Bickler, Tetrahedron Lett. 1997, 38, 7325-7328;
54. d) M. F. Gordeev, G. W. Luehr, H. C. Hui, E. M. Gordon, D. V. Patel, Tetrahedron 1998, 54, 15879-15890.
55. a) E. G. Brown, J. M. Nuss, Tetrahedron Lett. 1997, 38, 8457-8460;
56. b) D. S. Brown, J. M. Revill, R. E. Shute, Tetrahedron Lett. 1998, 39, 8533-8536.
57. An acidolyzable handle based on indole-3-carboxaldehyde was reported recently: K. G. Estep, C. E. Neipp, L. M. S. Stramiello, M. D. Adam, M. P. Allen, S. Robinson, E. J. Roskamp, J. Org. Chem. 1998, 63, 5300-5301.