Synthesis and application of N,N-bis-(1-adamantyloxycarbonyl) amino acids.
The preparation of novel bis-(1-adamantyloxycarbonyl) amino acid derivatives has been undertaken and their properties studied. Among them, the p-nitrophenyl esters were subsequently applied to the stepwise synthesis of Leu-enkephalin. In the last coupling step, some hydantoin formation was encountered but it could be nearly completely overcome by working with more concentrated solution. The preparation of a tyrosine derivative presented special problems owing to the existence of the phenolic group in the precursor. The relative stability of 1-adamantyloxycarbonyl as N- and O-protecting groups was also studied.
Nyasse
B
B
Department of Biochemistry, University of Uppsala, Sweden.
Ragnarsson
U
U
D000218:Adamantane / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D000595:Amino Acid Sequence; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004743:Enkephalin, Leucine / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D014443:Tyrosine / Q000031:analogs & derivatives
D014443:Tyrosine; D004743:Enkephalin, Leucine; D000218:Adamantane