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Synthesis and Biological Properties of Enkephalin-like Peptides Containing Adamantylalanine in Position 4 and 5

✍ Scribed by Kim Quang Do; Robert Schwyzer

Publisher
John Wiley and Sons
Year
1981
Tongue
German
Weight
356 KB
Volume
64
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The syntheses of seven [D‐ala‐^2^]‐enkephalin analogues, H‐Tyr‐ala‐Gly‐X‐Y, with X‐Y = Phe‐Ada‐OH, Phe‐ada‐OH, Phe‐Ada‐NH~2~, Phe‐ada‐NH~2~, Ada‐Leu‐OH, Ada‐Leu‐NH~2~, and Ada‐Ada‐NH~2~ are described. The compounds with Y = Ada (= L‐Ada) or ada (= D‐Ada) show pronounced morphine‐like activities in certain bioassays, whereas those with X = Ada were most inactive. The analogues were used to explore the influence of steric, electronic, and hydrophobic properties of the side chains of X and Y on opioid activity (see [14]).

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