Design and Synthesis of 1-Aminocycloalkane-1-carboxylic Acid-Substituted Deltorphin Analogues: Unique δ and μ Opioid Activity in Modified Peptides-Reference-Cited by-同舟云学术

Design and Synthesis of 1-Aminocycloalkane-1-carboxylic Acid-Substituted Deltorphin Analogues: Unique δ and μ Opioid Activity in Modified Peptides

Published:1996-01-01 Issue:3 Volume:39 Page:773-780
ISSN:0022-2623
Container-title:Journal of Medicinal Chemistry
language:en
Short-container-title:J. Med. Chem.

Author:

Breveglieri Angela¹,Guerrini Remo¹,Salvadori Severo¹,Bianchi Clementina¹,Bryant Sharon D.¹,Attila Martti¹,Lazarus Lawrence H.¹

Affiliation:

1. Department of Pharmaceutical Sciences and Institute of Pharmacology, University of Ferrara, I-44100 Ferrara, Italy, Peptide Neurochemistry Section, National Institute of Environmental Health Sciences, Research Triangle Park, North Carolina 27709, and Department of Pharmacy, Division of Pharmacology and Toxicology, University of Helsinki, SF-00014 Helsinki, Finland

Publisher

American Chemical Society (ACS)

Subject

Drug Discovery,Molecular Medicine

Link

https://pubs.acs.org/doi/pdf/10.1021/jm950490j

Reference51 articles.

1. Symbols and abbreviations are in accord with the recommendations of the IUPAC-IUB Commission on Nomenclature (J. Biol. Chem.1972,247, 977). Other abbreviations: Acxc, Cα,α-dialkylated α-amino acids (1-aminocycloalkane-1-carboxylic acid) (hexane,x= 6; pentane,x= 5; propanex= 3); Boc,tert-butoxycarbonyl; Boc2O, Boc-anhydride (di-tert-butyl dicarbonate); DCC, dicyclohexylcarbodiimide; DIPCDI, 1,3-diisopropylcarbodiimide; DMSO, dimethyl sulfoxide; DMF,N,N-dimethylformamide; EDC, ethyldicarbodiimide; Fmoc, (fluoren-9-ylmethoxy)carbonyl; HOBt, 1-hydroxybenzotriazole; IBCF, isobutyl chloroformate; OtBu,tert-butyl ester;1H-NMR, proton nuclear magnetic resonance spectrometry; Rink resin, 4-(2‘,4‘-dimethoxyphenyl)-Fmoc-aminomethylphenoxy-resin; TEA, triethylamine; TFA, trifluoroacetic acid; Z, benzyloxycarbonyl.

2. The opioid peptides of the amphibian skin

3. The toad, ugly and venomous, wears yet a precious jewel in his skin

4. Frog skin opioid peptides: a case for environmental mimicry.

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