Acid-labile anchoring linkages for solid phase synthesis of C-terminal asparagine peptides using the Fmoc strategy.
Two acid-labile substituted benzylamine type anchoring linkages, 4-benzoxy-2,6-dimethoxybenzylamine and 2-benzoxy-4,6-dimethoxybenzylamine, for solid phase synthesis of peptide amides were prepared. The Na-9-fluorenylmethyloxycarbonyl (Fmoc) amino acids could be easily attached to the resins with DCC/HOBt (loading 0.5-0.6 mmol/g resin). After final removal of the Na-protecting groups, treatment with TFA (50-95%) yielded amino acid and peptide amides in high purity. As we could show for the synthesis of thymulin (FTS, pGlu-Ala-Lys-Ser-Gln-Gly-Gly-Ser-Asn), these two resins with anchoring linkages are well suited for the synthesis of C-terminal Asn peptides using protected aspartic acid derivative as starting material.
Shao
J
J
Department of Physical Biochemistry, University of Tübingen, FRG.
Li
Y H
YH
Voelter
W
W
D000595:Amino Acid Sequence; D000596:Amino Acids; D001216:Asparagine; D005449:Fluorenes; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis*; D012117:Resins, Synthetic / Q000138:chemical synthesis*; D013935:Thymic Factor, Circulating / Q000138:chemical synthesis
D000596:Amino Acids; D005449:Fluorenes; D007202:Indicators and Reagents; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010455:Peptides; D012117:Resins, Synthetic; D001216:Asparagine; D013935:Thymic Factor, Circulating