Literature DB >> 5260928

Acetylcholine and its thiolester and selenolester analogs: conformation, electron distribution, and biological activity.

E Shefter, H G Mautner.   

Abstract

The crystal structures of acetylthiolcholine bromide and propionylthiolcholine iodide were elucidated. Acetylthiolcholine was found to be essentially isosteric with acetylselenolcholine, while the conformation of these compounds was quite different from that of acetylcholine. The importance of conformation and electron distribution in the biological actions of choline esters is discussed.

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Year:  1969        PMID： 5260928      PMCID： PMC223458          DOI： 10.1073/pnas.63.4.1253

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  17 in total

1.  The crystal and molecular structure of 2,4-dithiouracil.

Authors:  E Shefter; H G Mautner
Journal:  J Am Chem Soc       Date:  1967-03-01       Impact factor: 15.419

2.  Crystal structure of thiolphthalide.

Authors:  E Shefter
Journal:  J Pharm Sci       Date:  1968-01       Impact factor: 3.534

3.  Similarity of effects of oxygen, sulfur, and selenium isologs on the acetylcholine receptor in excitable membranes of junctions and axons.

Authors:  P Rosenberg; H G Mautner; D Nachmansohn
Journal:  Proc Natl Acad Sci U S A       Date:  1966-04       Impact factor: 11.205

4.  Crystal and molecular structure of acetylselenocholine iodide.

Authors:  E Shefter; O Kennard
Journal:  Science       Date:  1966-09-16       Impact factor: 47.728

5.  Sulfur and selenium compounds related to acetylcholine and choline. VI. Effects of homocholine derivatives on the electroplax preparation.

Authors:  G D Webb; H G Mautner
Journal:  Biochem Pharmacol       Date:  1966-12       Impact factor: 5.858

6.  Molecular orbital calculation of preferred conformations of acetylcholine, muscarine, and muscarone.

Authors:  L B Kier
Journal:  Mol Pharmacol       Date:  1967-09       Impact factor: 4.436

7.  Chemical structure and function of the active center of acetylcholinesterase.

Authors:  R M Krupka
Journal:  Biochemistry       Date:  1966-06       Impact factor: 3.162

8.  Structure of acetylcholine and other substrates of cholinergic systems.

Authors:  F G Canepa; P Pauling; H Sörum
Journal:  Nature       Date:  1966-05-28       Impact factor: 49.962

9.  ANALOGS OF PARASYMPATHETIC NEUROEFFECTORS. II. COMPARATIVE PHARMACOLOGICAL STUDIES OF ACETYLCHOLINE, ITS THIO AND SELENO ANALOGS, AND THEIR HYDROLYSIS PRODUCTS.

Authors:  K A SCOTT; H G MAUTNER
Journal:  Biochem Pharmacol       Date:  1964-06       Impact factor: 5.858
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  2 in total

Review 1.  End-plate acetylcholine receptor: structure, mechanism, pharmacology, and disease.

Authors:  Steven M Sine
Journal:  Physiol Rev       Date:  2012-07       Impact factor: 37.312

2.  Conformational relationships between analogs of acetylcholine and those of local anesthetics in solution.

Authors:  A Makriyannis; R F Sullivan; H G Mautner
Journal:  Proc Natl Acad Sci U S A       Date:  1972-11       Impact factor: 11.205
  2 in total

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