Methods to initiate synthetic re-structuring of peptides

Tetrahedron

Volumn 59, Issue 45, 2003, Pages 8947-8954

  Wei, Qi ^a   Harran, Susan ^a,b   Harran, Patrick G ^a  

^a UNIVERSITY OF TEXAS AT DALLAS   (United States)

^b Cumbre Inc   (United States)

Author keywords

Heterocycles; Palladium catalysis; Peptides; Rearrangements; Solid phase synthesis

Indexed keywords

PEPTIDE; POLYMER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; MACHINE; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0142186301     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.04.008     Document Type: Article

References (26)

1. Outlines of this general concept are also evident in Houghten's "Libraries from libraries experiments". See: Ostresh J.M., Husar G.M., Blondelle S.E., Dörner B., Weber P.A., Houghten R.A. Proc. Natl. Acad. Sci. USA. 91:1994;11138-11142.
2. Sisko J., Mellinger M., Sheldrake P.W., Baine N.H. Tetrahedron Lett. 37:1996;8113-8116.
3. (a) Sisko J., Kassick A.J., Mellinger M., Filan J.J., Allen A., Olsen M.A. J. Org. Chem. 65:2000;1516-1524
4. (b) van Leusen A.M., Wildeman J., Oldenziel O.H. J. Org. Chem. 42:1977;1153-1159.
5. Imidazole 4 is produced as an inconsequential mixture of diastereomers. This material, and others like it examined in this study ('condensation' products in Table 1) are highly insoluble in most common organic solvents as well as water. Preparative scale purification therefore is a challenge. Precipitation is found most effective although, because recovery using this method is not complete, isolated yields (Table 1) underestimate the true efficiency of these reactions.
6. For palladium catalysis relevant to this work see: (a) Trost, B. M.; Toste, F. D. Int. Pat. App. (PCT) Publication number WO 00/14033, 2000. (b) Trost B.M., Toste F.D. J. Am. Chem. Soc. 120:1998;9074-9075 (c) Trost B.M., Toste F.D. J. Am. Chem. Soc. 120:1998;815-816 (d) Goux C., Lhoste P., Sinou D. Synlett. 1992;725-727.
7. For palladium catalysis relevant to this work see: (a) Trost, B. M.; Toste, F. D. Int. Pat. App. (PCT) Publication number WO 00/14033, 2000. (b) Trost B.M., Toste F.D. J. Am. Chem. Soc. 120:1998;9074-9075 (c) Trost B.M., Toste F.D. J. Am. Chem. Soc. 120:1998;815-816 (d) Goux C., Lhoste P., Sinou D. Synlett. 1992;725-727.
8. For palladium catalysis relevant to this work see: (a) Trost, B. M.; Toste, F. D. Int. Pat. App. (PCT) Publication number WO 00/14033, 2000. (b) Trost B.M., Toste F.D. J. Am. Chem. Soc. 120:1998;9074-9075 (c) Trost B.M., Toste F.D. J. Am. Chem. Soc. 120:1998;815-816 (d) Goux C., Lhoste P., Sinou D. Synlett. 1992;725-727.
9. For palladium catalysis relevant to this work see: (a) Trost, B. M.; Toste, F. D. Int. Pat. App. (PCT) Publication number WO 00/14033, 2000. (b) Trost B.M., Toste F.D. J. Am. Chem. Soc. 120:1998;9074-9075 (c) Trost B.M., Toste F.D. J. Am. Chem. Soc. 120:1998;815-816 (d) Goux C., Lhoste P., Sinou D. Synlett. 1992;725-727.
10. 1H NMR and mass spectral data consistent with a symmetrical dimer.
11. (a) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043-6048.
12. (b) Kamer P.C.J., van Leeuwen P.W.N.M., Reek J.N.H. Acc. Chem. Res. 34:2001;895-904
13. (c) Kranenburg M., van der Burgt Y.E.M., Kamer P.C.J., van Leeuwen P.W.N.M. Organometallics. 14:1995;3081-3089.
14. Peptides used in this study were prepared (Fmoc methodology) as C-terminal n-butyramides to approximate the size and hydrophobicity of a spacer used for solid-phase synthesis experiments (Scheme 3).
15. 2/ 5 complex. While initial studies have focused on peptides containing N-terminal Gly or Ala residues, we see no indication of a limited tolerance at this position.
16. 3OD) of the β-styryl proton in 11 (C16H, δ 6.37) is more similar to that observed in 25-membered macrocycles ( 7-10, 13, 16, 17 - range: δ 6.29-6.45) than it is to the 22-membered ring series [namely 6 (δ 6.16) and 14 (δ 6.21)]. The minor isomer (assigned as 12 ) has this resonance appearing at δ 6.15.
17. 1/2∼5 h) when re-subjected to the same conditions used for its synthesis. Aqueous cyanide minimizes product loss by poisoning the etherification catalyst.
18. Williams A.J., Uto Y., Wipf P., Reno M.J., Williams D.R. Org. Lett. 2:2000;1165-1168.
19. Dihydroxylation using 'Super AD-mix-β' (Ref. 14) provides glycol 18 as a mixture (94:6) of diastereomers. The stereochemistry of the major isomer (shown) is assigned using an established mnemonic. The use of Super AD-mix-α provides the same two diols (confirmed by HPLC co-injection) but in a 92:8 ratio in which 18 is minor.
20. Nicolaou K.C., Yue E.W., La Greca S., Nadin A., Yang Z., Leresche J.E., Tsuri T., Naniwa Y., De Riccardis F. Chem. Eur. J. 1:1995;467-494.
21. Aryl Claisen rearrangement is best performed by microwave heating (180°C, 40 min) solutions of 8 containing flash chromatography-grade silica gel (230-400 mesh, 4 g/mmol 8 ). Added silica gel allows the reaction to proceed to full conversion without substantial degradation. Soluble Lewis-acidic additives have thus far failed in this regard.
22. Chatterjee A.K., Morgan J.P., Scholl M., Grubbs R.H. J. Am. Chem. Soc. 122:2000;3783-3784.
23. In this discussion, 'alkaloid-like' is meant primarily to contrast 'peptide-like' Our goal is the systematic preparation, from peptides, of non-reactive molecules that passively diffuse into the cytoplasm of living cells from culture media.
24. Professor Matthew Shair (Harvard University) generously provided us with resin that fueled our initial experiments. See: Tallarico J.A., Depew K.M., Pelish H.E., Westwood N.J., Lindsley C.W., Shair M.D., Schreiber S.L., Foley M.A. J. Comb. Chem. 3:2001;312-318.
25. Chan W.C., White P.D. Fmoc Solid Phase Peptide Synthesis. 2000;Oxford University, Oxford. ISBN 0199637245.
26. 3OH. Achieving complete conversion in the synthesis of 25 from 24 is the subject of ongoing experiments.