Leucine enkephalin → HCID 88357735, compound

Participants

Reaction Steps

Reaction of YGGFL with Dimethylaminopropylamine and Thiocarbonyldiimidazole. Dimethylaminopropylamine (1 μmol in 50 μl of DMF) was added to 1,1'-thiocarbonyldiimidazole (1 μmol in 50 μl DMF) and allowed to react for five minutes at 25° C. The pentapeptide, YGGFL (100 nmol in 50 μl DMF), was added and allowed to react for twenty minutes at 25° C. The sample was then taken to dryness in a vacuum centrifuge, redissolved in 0.1% trifluoroacetic acid in water (100 μl), and analyzed by reversed phase HPLC (FIG. 6). The expected peptide product (the N-terminal dimethylaminopropylthiourea derivative; peak B) was identified by FAB/MS (MH+=700) and obtained in approximately 95% yield. Peak A is the starting peptide, YGGFL (MH+=556). Peak B was then treated with 50 μl of anhydrous trifluoroacetic acid for ten minutes at 50° C., dried in a vacuum centrifuge, redissolved in 0.1% trifluoroacetic acid in water (100 μl), and analyzed by reversed phase HPLC. The shortened peptide (GGFL) (MH+=393) and the dimethylaminopropyl thiocarbamyl amino acid (MH+=326) were found in quantitative yield. No dimethylaminopropyl thiohydantoin tyrosine was obtained.

Provenance & Evidence