Polymeric 2-mercaptopyridine and 2-mercapto-nitrobenzene derivatives. New reagents for peptide synthesis.
Insoluble 2-mercaptopyridine and 2-mercapto-nitrobenzene derivatives were prepared by modification of commercially available polystyrene. Applicability of these polymers as reagents for the thiolytic removal of the 2-nitrophenylsulphenyl amino-protecting group and as supports for preparation of polymeric active esters was evaluated. Polymeric 2-mercaptopyridine (PMP) was found efficient for both purposes. It was used in the stepwise synthesis of Leu-enkephalin via the polymeric reagent approach, serving as an Nps-cleaver. Polymeric esters derived from PMP and Boc-amino acids proved to be excellent acylators. Their usefulness is exemplified in the preparation of two dipeptides, which were produced rapidly and in high yields and purity.
D004723:Endorphins / Q000138:chemical synthesis*; D004743:Enkephalin, Leucine; D004745:Enkephalins / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009578:Nitrobenzenes; D011108:Polymers; D011725:Pyridines; D013438:Sulfhydryl Compounds
D004723:Endorphins; D004745:Enkephalins; D007202:Indicators and Reagents; D009578:Nitrobenzenes; D011108:Polymers; D011725:Pyridines; D013438:Sulfhydryl Compounds; D004743:Enkephalin, Leucine