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Arginine-Rich Molecular Transporters for Drugs 145<br />

TABLE 7.1<br />

All Possible Permutations of the Insertion of between One and Six<br />

Aminocaproic Acids (aca) into a Heptamer of Arginine<br />

code code code<br />

1 0 RRRRRRR 23 3.1 RacaRacaRacaRRRR 43 4.1 RacaRacaRacaRacaRRR<br />

2 1.1 RacaRRRRRR 24 3.2 RacaRacaRRacaRRR 44 4.2 RacaRacaRacaRRacaRR<br />

3 1.2 RRacaRRRRR 25 3.3 RacaRacaRRRacaRR 45 4.3 RacaRacaRacaRRRacaR<br />

4 1.3 RRRacaRRRR 26 3.4 RacaRacaRRRRacaR 46 4.4 RacaRacaRRacaRacaRR<br />

5 1.4 RRRRacaRRR 27 3.5 RacaRRacaRacaRRR 47 4.5 RacaRacaRRacaRRacaR<br />

6 1.5 RRRRRacaRR 28 3.6 RacaRRacaRRacaRR 48 4.6 RacaRacaRRRacaRacaR<br />

7 1.6 RRRRRRacaR 29 3.7 RacaRRacaRRRacaR 49 4.7 RacaRRacaRacaRacaRR<br />

8 2.1 RacaRacaRRRRR 30 3.8 RacaRRRacaRacaRR 50 4.8 RacaRRacaRacaRRacaR<br />

9 2.2 RacaRRacaRRRR 31 3.9 RacaRRRacaRRacaR 51 4.9 RacaRRacaRRacaRacaR<br />

10 2.3 RacaRRRacaRRR 32 3.10 RacaRRRRacaRacaR 52 4.10 RacaRRRacaRacaRacaR<br />

11 2.4 RacaRRRRacaRR 33 3.11 RRacaRacaRacaRRR 53 4.11 RRacaRacaRacaRacaRR<br />

12 2.5 RacaRRRRRacaR 34 3.12 RRacaRacaRRacaRR 54 4.12 RRacaRacaRacaRRacaR<br />

13 2.6 RRacaRacaRRRR 35 3.13 RRacaRacaRRRacaR 55 4.13 RRacaRacaRRacaRacaR<br />

14 2.7 RRacaRRacaRRR 36 3.14 RRacaRRacaRacaRR 56 4.14 RRacaRRacaRacaRacaR<br />

15 2.8 RRacaRRRacaRR 37 3.15 RRacaRRacaRRacaR 57 4.15 RRRacaRacaRacaRacaR<br />

16 2.9 RRacaRRRRacaR 38 3.16 RRacaRRRacaRacaR 58 5.1 RacaRacaRacaRacaRacaRR<br />

17 2.10 RRRacaRacaRRR 39 3.18 RRRacaRacaRacaRR 59 5.2 RacaRacaRacaRacaRRacaR<br />

18 2.11 RRRacaRRacaRR 40 3.19 RRRacaRacaRRacaR 60 5.3 RacaRacaRacaRRacaRacaR<br />

19 2.12 RRRacaRRRacaR 41 3.20 RRRacaRRacaRacaR 61 5.4 RacaRacaRRacaRacaRacaR<br />

20 2.13 RRRRacaRacaRR 42 3.21 RRRRacaRacaRacaR 62 5.5 RacaRRacaRacaRacaRacaR<br />

21 2.14 RRRRacaRRacaR 63 5.6 RRacaRacaRacaRacaRacaR<br />

22 2.15 RRRRRacaRacaR 64 6.1 RacaRacaRacaRacaRacaRacaR<br />

Note: The individual peptides are referred to using codes that also include the number of substitutions<br />

in their format.<br />

as previously described. The peptides were cleaved from the resin using trifluoroacetic<br />

acid, purified by reverse phase HPLC, and their structure confirmed using<br />

electrospray mass spectrometry (Applied Biosystems, Foster City, CA).<br />

7.2.4 PEPTOID POLYAMINE SYNTHESIS<br />

Peptoids were synthesized manually using a fritted glass apparatus and positive<br />

nitrogen <strong>press</strong>ure for mixing the resin following the literature procedure developed<br />

by Zuckerman. 3,5,6 Treatment of Fmoc-substituted Rink amide resin (0.2 mmol) with<br />

20% piperidine/DMF (5 ml) for 30 min (2×) gave the free resin-bound amine, which<br />

was washed with DMF (3 × 5 ml). The resin was treated with a solution of bromoacetic<br />

acid (2.0 mmol) in DMF (5 ml) for 30 min. This procedure was repeated.<br />

The resin was then washed (3 × 5 mL DMF) and treated with a solution of mono-<br />

Boc diamine (8.0 mmol) in DMF (5 ml) for 12 h. These two steps were repeated<br />

until an oligomer of the required length was obtained. (Note: the solution of mono-<br />

Boc diamine in DMF could be recycled without appreciable loss of yield.) The resin<br />

was then treated with N-Fmoc-aminohexanoic acid (2.0 mmol) and DIC (2.0 mmol)

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