Fmoc strategy

As an alternative strategy, prelipidated building blocks can be used to generate prenylated peptides (Scheme 8). Thereby advantage is taken of the stability of the thioether linkage that offers the possibility of applying, for example, the Fmoc strategy for such peptides. Short N-Ras C-termini, for example, are readily available via this method. ... 

Table 1 Optimized Protocol of the Synthesis of Selenocysteine Peptides on Rink-Amide-MBHA Resin According to the Fmoc Strategy 10 ...

As shown in the purification of rat histone H2A1 53 amide synthesized using the FMOC strategy, remarkable results using a Pharmacia Biotech Mono S column were obtained for the purification of complex synthetic mixtures (Figures 3 and 4)J5H] This system has been used with similar success with several other peptides. With a complex mixture of peptide/proteins, ion-exchange chromatography was found to be an important first step for preliminary fractionation to be further purified by RP-HPLC. 

Purification of Rat Histone H2A1 53-NH2 Synthesized Using the Fmoc Strategy 58 ... 

Fmoc Strategy Procedure for TOAC-Containing Peptides 127 ... 

Peptides with up to 166 amino acids (aglycon of erythropoietin [34]) have been prepared using the Fmoc strategy on cross-linked polystyrene. The preparation of peptides containing several /V-methylamino acids (e.g. cyclosporine [35,36]) has also been successfully performed using Fmoc protection. Flowever, such difficult peptides require careful planning of the synthesis and often the use of special coupling techniques. 

Figure 16.4. Solid-phase peptide synthesis using the Fmoc strategy.

Some amino acids contain functional groups that need to be masked during peptide synthesis. Protective groups suitable for the Boc strategy must be resistant towards TFA, whereas for the Fmoc strategy stability towards piperidine must be ensured. 

The linear decapeptide was synthesized on Fmoc-Lys(Boc)-SASRIN-resin (2.0 g, substitution 0.6 mmol-g1) applying standard Fmoc strategy based on DIC/HOBt activation with DIPEA as base. After removal of the last Fmoc group, the peptide was cleaved from the resin and cyclized as described in Section 13.1.1.1.1 yield 0.671 g (68%) ESI-MS 1646.3 [M + H]+, 823.8 [M/2+H]+. 

Solid-phase synthesis of the peptide was carried out manually on a Rink amide resin (435 mg, substitution level 0.46 mmol -g 1) applying the Fmoc strategy. After removal of the Fmoc group attached to the resin with 20% piperidine in DMF (20 min), Fmoc-Tyr(tBu)-OH (230 mg, 0.5 mmol) was introduced with DIC (78 pL, 0.5 mmol) in the presence of HOBt (68 mg, 0.5 mmol) (reaction time 2h). After... 

Wakamiya, T Saruta, K., Yasuoka, J and Kusumoto, S. (1994) An efficient procedure for solid-phase synthesis of phosphopeptides by the Fmoc strategy. Chem. Lett. 1099-1102. 

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