By Irving Wainer

ISBN-10: 0824788192

ISBN-13: 9780824788193

McGill collage, Montreal, Quebec. medical Pharmacology, quantity 18. re-creation of a textual content at the stereoisomeric composition of drug components as a side within the improvement, approval, and scientific use of prescription drugs. 19 participants, thirteen U.S. DNLM: Chemistry Pharmaceutical - tools.

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Example text

Later qualified, modified, and generalized by others, Pasteur's new method became applicable to the separation of a number of other racemates (8). Pasteur then ends his second lecture with the following: Such, gentlemen, are in co-ordinated formthe investigations whichI have been asked to present to you. " It is, in fact, the theory of molecular asymmetrythat we havejust established, oneof the most exalted chapters of the science. It was completely unforeseen, and opens to physiology new horizons, distant, but sure.

Because each of these sets of stereoisomers contains no optically active members, these compounds are classified as geometrical isomers. This situation is illustrated by 2-butene (Fig. 6). H \CH3 >,=c /H /C "> H,= 3C CH3 c&- or 2-isomer H' trans- or €-isomer FIGURE6 Theisomers of 2-butene. nd Terms Stereochemical 31 In thismolecule, thetwo methyl groups can be found on the same or opposite sidesof the double bond. When they are on the same side, the cis or Z isomer; when they are on the opposite molecule is defined as the sides, thetrans or E designation is used.

A. The Fischer Convention The Fischer convention was designed by Emile Fischer in 1919 (3). in7. Recent x-ray crystallographic studies have established that the assigned configuration is, in fact, correct. To assign a configuration, the molecule under investigation must be chemically converted to glyceraldehyde or another molecule of known configuration. For example, Lalanine has a(+) sign of rotation, whereas the signof rotation for Lglyceraldehydeis (-). For sugars, which contain a number of asymmetric centers, and fordiastereomerswithonly two centers,theFischerconvention defines a series asD or L according to whether the configuration at the highest numbered asymmetric center is analogousDto or Lglyceralde- Walner and Marcotte 32 CH0 HOC -H - I l l 1 D-(+)-glyceraldehyde L-(-)-glyceraldehyde HC -O -H 2OH CH2OH CH0 'CH0 H~-CO -H H3C - I I I HO~-CH - -OH I I H'C-OH I 4CH20H 4CH20H D-erythrose D- t hreose FIGURE7 The configurations of D-(+) and L(-)-glyceraldehyde, D-erythrose, and D-threose, accordingto the Fischer Convention.

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Drug Stereochemistry. Analytical Methods and Pharmacology by Irving Wainer


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