Synthesis of hydrophobic peptides: An Fmoc 'solubilising tail' method

Tetrahedron Letters

Volumn 39, Issue 16, 1998, Pages 2417-2420

  Choma, Christin T ^a   Robillard, George T ^a   Englebretsen, Darren R ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDE DERIVATIVE;

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHOBICITY; PEPTIDE SYNTHESIS; PROTEIN PURIFICATION; REACTION ANALYSIS; SOLUBILIZATION;

EID: 0032537163     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00214-7     Document Type: Article

References (16)

1. 1. Englebretsen, D.R. and Alewood, P.F. Tetrahedron Lett., 1996, 37, 8431-8434
2. 2. Schnölzer, M., Alewood, P., Jones, A., Alewood, D., Kent, S.B.H. Int. J. Peptide Protein Research 1992, 40, 180-193
3. 3. A Perkin Elmer AB1 433A peptide synthesiser using Fastmoc® peptide synthesis protocols was used for peptide synthesis. Amino acid side chain protecting groups used were Cys(Trt), Cys(acm) His(Trt), Lys(Boc), Ser(tBu), Arg(Pmc), Asp(OtBu), Glu(OtBu), Asn(Trt), Gln(Trt), Tyr(tBu), Thr(tBu). Unprotected Trp was used in the synthesis of peptide 1, whereas peptides 3-5 were synthesised using Trp(Boc). Novabiochem amide linker resin was used for all syntheses. Dried peptide-resin was cleaved with a mixture of TFA:water:thioanisole: EDT:phenol 40:2:2:1:3 v/v/v/v/w (1); water: TFA 5:95 v/v (2), or water:EDT: TFA 2.5:2.5:95 v/v/v (3-5). The crude ether-precipitated peptides were worked up using normal procedures.
4. 4. a) Atherton, E., Logan, C.J., and Sheppard, R.C. J. Chem. Soc. Perkin 1, 1981, 538-546,
5. b) Renil, M. and Meldal, M. Tetrahedron Lett. 1995, 36, 4647-4650,
6. c) Volkmer-Engert, R., Hoffman, B., and Schneider-Mergener, J. Tetrahedron Lett., 1997, 38, 1029-1032
7. 5. a) Baleux, F., Calas, B., and Mery, J. Int. J. Peptide Protein Res. 1986, 28, 22-28,
8. b) Suich, D.J., Ballinger, M.D., Wells, J.A., and DeGrado, W.F. Tetrahedron Lett., 1996, 37, 6653-6656
9. 6. Gisin, B.F. Helvetica Chimica Acta, 1973, 56, 1476-1482
10. 7. The anhydride of 4-bromomethylbenzoic acid was coupled to the amine of the resin-bound tail peptide. The 4-Hmb ester linkage was formed by reacting overnight 4 eq of the cesium salt of Fmoc-amino acid with the bromomethyl-group of the linker. Ninhydrin test of the resulting resin showed partial removal of the Fmoc group, however HPLC analysis of crude cleaved peptides after the syntheses generally revealed only low levels of unwanted side products.
11. 6-amide, mass 1612.7 Da, to be present).
12. 9. Bedford, J., Hyde, C. Johnson, T., Jun, W., Quibell, M., and Sheppard, R.C. Int. J. Peptide Protein Res. 1992, 40, 300-307
13. 10. Merrifield, R.B., Singer, J., and Chait, B.T. Analytical Biochemistry, 1988, 174, 399-414
14. 11. a) Johnson, T., Quibell, M., Owen, D., and Sheppard, R.C. J. Chem. Soc. Chem. Comms. 1993, 369-372,
15. b) Simmonds, R.G. Int. J. Peptide Protein Res. 1996, 47, 36-41
16. 12. Olivera, E., Miranda, A., Albericio, F., Andreu, D., Paiva, A.C.M., Nakaie, C.R., and Tominga, M. Int. J. Peptide Protein Res. 1997, 49, 300-307