A measure of solvent effects on swelling of resins for solid phase organic synthesis

Tetrahedron Letters

Volumn 39, Issue 49, 1998, Pages 8951-8954

  Santini, Richard ^a   Griffith, Michael C ^a   Qi, Ming ^a  

^a Trega Biosciences Inc   (United States)

Author keywords

Resins; Solid phase synthesis; Solvent and solvent effects

Indexed keywords

RESIN; SOLVENT;

ARTICLE; CHEMICAL ANALYSIS; ORGANIC CHEMISTRY; SYNTHESIS;

EID: 0032480960     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02069-3     Document Type: Article

References (16)

1. 1. Fields, G. B. Ed., Solid-Phase Peptide Synthesis, Academic Press: San Diego; 1997.
2. 2. Merrifield, R. B. J. Am. Chem. Soc. 1963, 55, 2149-2154.
3. 3. Balkenhohl, F.; Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int., Ed. Engl. 1996, 35, 2289-2337.
4. 4. Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555-600.
5. 5. Special Issue on Combinatorial Chemistry, Czarnik, A. W.; Ellman, J. A. Eds., Acc. Chem. Res. 1996, 29, 111-170.
6. 6. Combinatorial Chemistry, Szostak, J. Ed., Chem. Rev. 1997, 97, 347-510.
7. 7. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643-5678.
8. 8. Wilson, S. R.; Czarnik, A. W. Eds., Combinatorial Chemistry, Synthesis and Application, John Wiley & Sons: New York; 1997.
9. 9. Fields, G. B.; Fields, C. G. J. Am. Chem. Soc. 1991, 113, 4202-4207.
10. 10. Thaler, A.; Seebach, D.; Cardinaux, F. Helv. Chim. Acta 1991, 74, 628-643.
11. 11. Cilli, E. M.; Oliveira, E.; Marchetto, R.; Nakaie, C. R. J. Org. Chem. 1996, 61, 8992-9000.
12. 12. Hall, P. J.; Galan, D. G.; Machado, W. R.; Mondragon, E. B. B.; Sherrington, D. C.; Calo, J. M. J. Chem. Soc., Faraday Trans. 1997, 93, 463-466.
13. 13. Arshady, R. Makromol. Chem. 1988, 189, 1295-1303.
14. 14. Pugh, K. C.; York, E. J.; Stewart, J. M. Int. J. Peptide Protein Res. 1992, 40, 208-213.
15. 15. Sarin, V. K.; Kent, S. B. H.; Merrifield, R. B. J. Am. Chem. Soc. 1980, 102, 5463-5470.
16. 16. All of the resins used are bought from NovaBiochem except TentaGel S Ram which supplied by RAPP Polomere; they are in 100-200 mesh particle size, except Trityl resin which is 200-400 mesh and contain 1% DVB cross-linking except one of the Wang resin and MBHA containing 2% DVB. Neutral MBHA were obtained by washing the MBHA HCl resin with DCM (1x), 5% DIEA/DCM (2x, 1 h each), DCM (2x), and MeOH (2x), and drying under vacuum. Loadings (mmol/g) for Wang (low loading) 0.60, Wang (HL) 1.16, Wang (2% DVB) 0.75, TentaGel S Ram 0.30, MBHA 0.80, Merrifield 0.95, Trityl 0.84, Rink amide 0.57.