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The Molecular Structure of Penicillin

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Ronald Bentley

Department of Biological Sciences, University of Pittsburgh, Pittsburgh, PA 15260

J. Chem. Educ., 2004, 81 (10), p 1462

DOI: 10.1021/ed081p1462

Publication Date (Web): October 1, 2004

Section:

History, Education, and Documentation

Abstract

The chemical structure of penicillin was determined between 1942 and 1945 under conditions of secrecy established by the U.S. and U.K. governments. The evidence was not published in the open literature but as a monograph. This complex volume does not present a structure proof that can be readily comprehended by a student. In this article, a basic structural proof for the penicillin molecule is provided, emphasizing the chemical work. The stereochemistry of penicillin is also described, and various rearrangements are considered on the basis of the accepted β-lactam structure.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Subject):

Drugs / Pharmaceuticals

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Received: August 03, 2009

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The Molecular Structure of Penicillin

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The Total Synthesis of Penicillin V

An Intuitive Look at the Relationship of Ki and IC50: A More General Use for the Dixon Plot

endo- and exo-Stereochemistry in the Diels-Alder Reaction: Kinetic versus Thermodynamic Control

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