The First Solid-Phase Synthesis of Oligomeric α-Aminooxy Peptides

Abstract

α-Aminooxy pentapeptides were synthesized on solid support by a stepwise monomer assembly in 40-65% purity of crude products, using the phthaloyl protected monomers.

Key words

α-aminooxy peptides - coupling - deprotection - solid-phase synthesis - solid support

References

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3

Baek, B.-h.; Lee, M.-r.; Kim, K. Y.; Cho, U.-I.; Boo, D. W.; Shin, I., manuscript in preparation.

4

Lee, M.-r.; Kim, K. Y.; Cho, U.-I.; Boo, D. W.; Shin, I., manuscript in preparation.

7

Burgess and coworkers reported solid-phase synthesis of oligoureas using phthaloyl protected isocyanate monomers. See ref. [6]

12

The natural tetrapeptide or α-aminooxy tetrapeptide in Tris-buffered saline (pH 7.4) containing 2% DMSO was incubated with trypsin at 37 °C. The retention time of natural tetrapeptide and α-aminooxy tetrapeptide (22.8 min and 24.1 min, respectively) was determined by analytic RP HPLC with a gradient of 5-95% CH₃CN in water (0.1% TFA) over 40 min (flow rate, 1.0 mL/min). The digested Ac-Phe-Lys-OH and H-Phe-Leu-OH were eluted at 15.9 minutes and 17.9 minutes under the same elution conditions described above.