Four F-alkylated muramyl dipeptides were synthesized by an efficient coupling reagent, Benzotriazol-1-yloxy-bis(pyrrolidino)carbo hexafluoro-phosphate(BBC)([1]).
Comparison of the reaction speed and yield with its analogues and some conventional peptide coupling reagents, pentafluorophenyl diphenylphosphate (FDP) was shown to be a more preferable ''active ester'...Comparison of the reaction speed and yield with its analogues and some conventional peptide coupling reagents, pentafluorophenyl diphenylphosphate (FDP) was shown to be a more preferable ''active ester'' type reagent for the peptide synthesis. The synthesis of oligopeptides using FDP was achieved with high yields. The influences of several reaction parameters such as solvent, base, additive and temperature on the coupling reaction were studied using HPLC method. The degree of racemization with FDP determined by HPLC or Young test was shown to be lower than that of DCCI. Octapeptide Gly-Cys(Bzl)-Ser-Gly-Lys-Leu-Ile-Cys(Bzl)-OH, corresponding to the amino acid sequence of gp41 of HIV-1, was successfully synthesized by 5+3 approach using FDP with high yield.展开更多
文摘Four F-alkylated muramyl dipeptides were synthesized by an efficient coupling reagent, Benzotriazol-1-yloxy-bis(pyrrolidino)carbo hexafluoro-phosphate(BBC)([1]).
基金supported by the National Natural Science Foundation of China and the State Key labortory of Bio-organic and Natural Products Chemistry.
文摘Comparison of the reaction speed and yield with its analogues and some conventional peptide coupling reagents, pentafluorophenyl diphenylphosphate (FDP) was shown to be a more preferable ''active ester'' type reagent for the peptide synthesis. The synthesis of oligopeptides using FDP was achieved with high yields. The influences of several reaction parameters such as solvent, base, additive and temperature on the coupling reaction were studied using HPLC method. The degree of racemization with FDP determined by HPLC or Young test was shown to be lower than that of DCCI. Octapeptide Gly-Cys(Bzl)-Ser-Gly-Lys-Leu-Ile-Cys(Bzl)-OH, corresponding to the amino acid sequence of gp41 of HIV-1, was successfully synthesized by 5+3 approach using FDP with high yield.
