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Synthesis and Biological Properties of Enkephalin‐like Peptides Containing Carboranylalanine in Place of Phenylalanine
Author(s) -
Schwyzer Robert,
Do Kim Quang,
Eberle Alex N.,
Fauchére JeanLuc
Publication year - 1981
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19810640712
Subject(s) - chemistry , steric effects , enkephalin , amide , stereochemistry , phenylalanine , amino acid , leu enkephalin , opioid peptide , side chain , opioid , combinatorial chemistry , biochemistry , organic chemistry , receptor , polymer
The syntheses of [ D ‐Ala 2 , Car 4 , Leu 5 ]‐enkephalin, its amide, and of [ D ‐Ala 2 , Car 4 , Met 5 ]‐enkephalin amide are described in detail. The three compounds show pronounced morphine‐like potencies in certain bio‐assays, and were used to investigate the influence of electronic, steric and hydrophobic properties of the side‐chains of amino acids no. 4 and 5 on opioid activity (see [13]).