DEUSS: A perdeuterated poly(oxyethylene)-based resin for improving HRMAS NMR studies of solid-supported molecules

Chemistry - A European Journal

Volumn 10, Issue 18, 2004, Pages 4532-4537

  Poschalko, Alexander ^b,f   Lancelot, Nathalie ^c   Marin, Julien ^a   Larras, Virginie ^d   Limal, David ^d,g   Elbayed, Karim ^c   Raya, Jesus ^c   Piotto, Martial ^e   Briand, Jean Paul ^a   Guichard, Gilles ^a   Bianco, Alberto ^a  

^a INSTITUT DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE   (France)

^b VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

^c UNIVERSITÉ DE STRASBOURG   (France)

^d Ecole Nationale Superieure de Chimie de Mulhouse   (France)

^e CNRS   (France)

^f DSM NUTRITIONAL PRODUCTS LTD   (Switzerland)

^g OM PHARMA   (Switzerland)

Author keywords

Combinatorial chemistry; NMR spectroscopy; Oligoureas; Peptides; Poly(oxyethylene); Resins

Indexed keywords

CHEMICAL REACTIONS; ETHYLENE; MOLECULES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; POLYMERS; PROTONS; SOLVENTS;

ACQUEOUS SOLUTIONS; ETHYLENE OXIDES (EO); NOVEL RESINS; RESIN-BOUND MOLECULES;

RESINS;

AMIDE; ANION; DEUTERIUM; EPICHLOROHYDRIN; ETHYLENE OXIDE; ORGANIC COMPOUND; PEPTIDE DERIVATIVE; POLOXAMER; POLYMER; POLYOXYETHYLENE DERIVATIVE; PROPYLENE; PROTON; RESIN; SOLVENT; UREA DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COVALENT BOND; CROSS LINKING; LIQUID; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARAMETER; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SIGNAL DETECTION; SOLID STATE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE;

ANION EXCHANGE RESINS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; POLYETHYLENE GLYCOLS;

EID: 4744338669     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400373     Document Type: Article

References (56)

1. a) B. Merrifield, J. Am. Chem. Soc. 1963, 85, 2149-2153;
2. b) B. Merrifield, Science 1986, 232, 341-347;
3. c) M. Goodman, A. Felix, L. Moroder, C. Toniolo, Methods of Organic Chemistry (Houben-Weyl), Vol. E22a, Thieme, Stuttgart, 2002.
4. a) S. D. Debenham, P. W. Snyder, E. J. Toone, J. Org. Chem. 2003, 68, 5805-5811;
5. b) J. M. Clough, R. V. H. Jones, H. McCann, D. J. Morris, M. Willis, Org. Biomol. Chem. 2003, 1, 1486-1497;
6. c) M. Meldal, Biopolymers 2002, 66, 93-100;
7. d) D. S. Thorpe, G. Rosse, H. Yeoman, S. Wilson, P. Willson, G. Harlow, A. Robinson, K. F. Wertman, Methods Mol. Biol. 2002, 201, 239-263;
8. e) C. Gibson, G. A. Sulyok, D. Hahn, S. L. Goodman, G. Holzemann, H. Kessler, Angew. Chem. 2001, 113, 169-173; Angew. Chem. Int. Ed. 2001, 40, 165-169;
9. e) C. Gibson, G. A. Sulyok, D. Hahn, S. L. Goodman, G. Holzemann, H. Kessler, Angew. Chem. 2001, 113, 169-173; Angew. Chem. Int. Ed. 2001, 40, 165-169;
10. f) S. Leon, R. Quarrell, G. Lowe, Bioorg. Med. Chem. Lett. 1998, 8, 2997-3002;
11. g) J. D. McBride, N. Freeman, G. J. Domingo, R. J. Leatherbarrow, J. Mol. Biol. 1996, 259, 819-827;
12. h) K. S. Lam, S. E. Salmon, E. M. Hersh, V. J. Hruby, W. M. Kazmierski, R. J. Knapp, Nature 1991, 354, 82-84;
13. i) H. M. Geysen, R. H. Meloen, S. J. Barteling, Proc. Natl. Acad. Sci. USA 1984, 81, 3998-4002.
14. a) W. Rapp, L. Zhang, R. Häbish, E. Bayer, Peptides 1988 (Eds.: G. Jung, E. Bayer), de Gruyter, Berlin, 1989, pp. 199-201;
15. b) E. Bayer, Angew. Chem. 1991, 103, 155-158; Angew. Chem. Int. Ed. Engl. 1991, 30, 113-129;
16. b) E. Bayer, Angew. Chem. 1991, 103, 155-158; Angew. Chem. Int. Ed. Engl. 1991, 30, 113-129;
17. c) M. Meldal, Tetrahedron Lett. 1992, 33, 3077-3080;
18. d) M. Renil, M. Meldal, Tetrahedron Lett. 1996, 37, 6185-6188;
19. e) J. Rademann, M. Grøtli, M. Meldal, K. Bock, J. Am. Chem. Soc. 1999, 121, 5459-5466.
20. a) W. L. Fitch, G. Detre, C. P. Holmes, J. N. Shoorlery, P. A. Keifer, J. Org. Chem. 1994, 59, 7955-7956;
21. b) A. Graven, M. Grøtli, M. J. Meldal, J. Chem. Soc. Perkin Trans. 1 2000, 955-962;
22. c) J. Furrer, M. Piotto, M. Bourdonneau, D. Limal, G. Guichard, K. Elbayed, J. Raya, J.-P. Briand, A. Blanco, J. Am. Chem. Soc. 2001, 123, 4130-4138;
23. d) C. W. Tornoe, M. Meldal, Tetrahedron Lett. 2002, 43, 6409-6411;
24. e) L. P. Miranda, W. D. Lubell, K. M. Halkes, T. Groth, M. Grøtli, J. Rademann, C. H. Gotfresden, M. Meldal, J. Comb. Chem. 2002, 4, 523-529;
25. f) N. Lancelot, K. Elbayed, J. Raya, M. Piotto, J.-P. Briand, F. Formaggio, C. Toniolo, A. Bianco, Chem. Eur. J. 2003, 9, 1317-1323;
26. g) P. Rousselot-Pailley, C. Boutillon, J.-M. Wieruszeski and G. Lippens, J. Pept. Sci. 2003, 9, 47-53;
27. h) M. Rainaldi, N. Lancelot, K. Elbayed, J. Raya, M. Piotto, J.-P. Briand, B. Kaptein, Q. B. Broxterman, A. Berkessel, F. Formaggio, C. Toniolo, A. Bianco, Org. Biomol. Chem. 2003, 1, 1835-1837.
28. a) A. Bianco, J. Furrer, D. Limal, G. Guichard, K. Elbayed, J. Raya, M. Piotto, J.-P. Briand, J. Comb. Chem. 2000, 2, 681-690;
29. b) J. Furrer, K. Elbayed, M. Bourdonneau, J. Raya, D. Limal, A. Bianco, M. Piotto, Magn. Reson. Chem. 2002, 40, 123-132.
30. C. D. Eisenbach, M. Peuscher, G. Wegner, M. Weiss, Makromol. Chem. 1983, 184, 2313-2323.
31. a) M. Salzmann, K. Pervushin, G. Wider, H. Senn, K. Wülthrich, Proc. Natl. Acad. Sci. USA 1998, 95, 13585-13590;
32. b) J. Fiaux, E. B. Bertelsen, A. L. Horwich, K. Wüthrich, Nature 2002, 418, 207-211;
33. c) V. Tugarinov, P. M. Hwang, J. O. Ollerenshow, L. E. Kay, J. Am. Chem. Soc. 2003, 125, 10420-10428.
34. O. Mitsunobu, Synthesis 1981, 1-28.
35. a) D. J. Rowlands, B. E. Clarke, A. R. Carroll, F. Brown, B. H. Nicholson, J. L. Bittle, R. A. Houghten, R. A. Lerner, Nature 1983, 306, 694-697;
36. b) L. L. France, P. G. Piatti, J. F. Newman, I. Toth, W. A. Gibbons, F. Brown, Proc. Natl. Acad. Sci. USA 1994, 91, 8442-8446;
37. c) M.-C. Petit, N. Benkirane, G. Guichard, A. Phan Chan Du, M. Marraud, M. T. Cung, J.-P. Briand, S. Muller, J. Biol. Chem. 1999, 274, 3686-3692.
38. a) S. H. Gellman, Acc. Chem. Res. 1998, 31, 173-180;
39. b) K. Kirshenbaum, R. N. Zuckermann, K. A. Dill, Curr. Opin. Struct. Biol. 1999, 9, 530-535.
40. N,N′-Linked oligoureas of seven and nine residues have be shown to adopt a 2.5 helical structure in solution. a) V. Semetey, D. Rognan, C. Hemmerlin, R. Graff, J.-P. Briand, M. Marraud, G. Guichard, Angew. Chem. 2002, 114, 1973-1975; Angew. Chem. Int. Ed. 2002, 41, 1893-1895;
41. N,N′-Linked oligoureas of seven and nine residues have be shown to adopt a 2.5 helical structure in solution. a) V. Semetey, D. Rognan, C. Hemmerlin, R. Graff, J.-P. Briand, M. Marraud, G. Guichard, Angew. Chem. 2002, 114, 1973-1975; Angew. Chem. Int. Ed. 2002, 41, 1893-1895;
42. b) C. Hemmerlin, M. Marraud, D. Rognan, R. Graff, V. Semetey, J.-P. Briand, G. Guichard, Helv. Chim. Acta 2002, 85, 3692-3711.
43. The chemical shift difference (Δδ) for the Cα protons of both residues in 6c is < 0.5 ppm. By comparison, geminal Cα protons of central residues in helical oligoureas (see Ref. [10]), exhibit large Δδ typically > 1 ppm.
44. G. Jung, Combinatorial Chemistry, Wiley-VCH, Weinheim, 1999.
45. C. Palomo, A. L. Palomo, F. Palomo, A. Mielgo, Org. Lett. 2002, 4, 4005-4008.
46. a) A. Johansson, E. Akerblom, K. Ersmark, G. Lindeberg, A. Hallberg, J. Comb. Chem. 2000, 2, 496-507;
47. b) B. A. Dressman, L. A. Spangle, S. W. Kaldor, Tetrahedron Lett. 1996, 37, 937-940.
48. J. Alsina, F. Albericio, Biopolymers 2003, 71, 454-477.
49. K. Elbayed, M. Bourdonneau, J. Furrer, T. Richert, J. Raya, J. Hirschinger, M. Piotto, J. Magn. Reson. 1999, 136, 127-129.
50. J. Neimark, J.-P. Briand, Pept. Res. 1993, 6, 219-228.
51. G. Guichard, V. Semetey, C. Didierjean, A. Aubry, J. P. Briand, M. Rodriguez, J. Org. Chem. 1999, 64, 8702-8705.
52. E. Kaiser, R. L. Colescott, C. D. Bossinger, P. I. Cook, Anal. Biochem. 1970, 34, 595-598.
53. L. Braunschweiler, R. R. Ernst, J. Magn. Reson. 1983, 53, 521-528.
54. J. Jeneer, B. H. Meier, P. Bachmann, R. R. Ernst, J. Chem. Phys. 1979, 71, 4546-4553.
55. G. Bodenhausen, D. J. Ruben, Chem. Phys. Lett. 1980, 69, 185-189.
56. A. J. Shaka, C. J. Lee, A. Pines, J. Magn. Reson. 1988, 77, 274-293.