Stable isolated symmetrical anhydrides of N alpha-9-fluorenylmethyloxycarbonylamino acids in solid-phase peptide synthesis. Methionine-enkephalin synthesis as an example.
The synthesis and isolation of symmetrical anhydrides of N alpha-9-fluorenylmethyloxycarbonyl (Fmoc) amino acids using water soluble carbodiimide is described. These compounds were used in a solid phase peptide synthesis of methionine-enkephalin on a p-benzyloxybenzyl ester polystyrene 1% divinylbenzene resin support. Homogeneous free pentapeptide was obtained in 42% overall yield. The Fmoc amino acid symmetrical anhydrides were stable during prolonged storage (2 years of 0 degrees) and offer advantages over present "Fmoc solid phase" methods which use anhydrides formed in situ.
D000596:Amino Acids / Q000138:chemical synthesis; D000812:Anhydrides / Q000138:chemical synthesis; D000818:Animals; D004723:Endorphins / Q000138:chemical synthesis*; D004744:Enkephalin, Methionine; D004745:Enkephalins / Q000138:chemical synthesis*; D005449:Fluorenes
D000596:Amino Acids; D000812:Anhydrides; D004723:Endorphins; D004745:Enkephalins; D005449:Fluorenes; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D004744:Enkephalin, Methionine