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Dehydro‐enkephalins

1983; Wiley; Volume: 21; Issue: 2 Linguagem: Inglês

10.1111/j.1399-3011.1983.tb03094.x

0367-8377

Yasuyuki Shimohigashi, James W. Dunning, Aldean J. Kolar, Charles H. Stammer,

Receptor Mechanisms and Signaling

Two kinds of dehydropeptide analogs of enkephalin containing a ΔTyr unit at the N ‐terminus have been synthesized by coupling Boc‐ΔTyr‐(Cl 2 Bzl)‐OH with amino acid amides and tetrapeptide esters using the water soluble carbodiimide‐HOBt method. Pentapeptides consisting of ΔTyr 1 , and ΔPhe 4 or ΔLeu 5 were also prepared. Ultraviolet difference spectroscopy was important in the characterization of the dehydro moieties, ΔTyr, ΔPhe and ΔLeu. Attempts to liberate ΔTyr 1 ‐enkephalins have been unsuccessful because of the instability of an N ‐terminal ΔTyr residue having p ‐phenolic group in the side chain.