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"Chiral Acetate": The Preparation, Analysis, and Applications of Chiral Acetic Acid

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Addison Ault

Department of Chemistry, Cornell College, Mount Vernon, IA 52314

J. Chem. Educ., 2003, 80 (3), p 333

DOI: 10.1021/ed080p333

Publication Date (Web): March 1, 2003

Abstract

I present a summary of the first reports of the preparation and analysis of "chiral acetate", versions of acetic acid that are chiral by virtue of the presence of the three isotopes of hydrogen on the methyl group: a proton, a deuteron, and a tritium atom. Next I describe how "chiral acetate" allows the determination of the steric course of the addition of acetate to malate, and the steric course of the biochemical formation and cleavage of citrate. I conclude with a review of two additional syntheses of "chiral acetate", and the use of this material in the determination of the steric course of the biochemical methyl transfer from (S)-adenosylmethionine (AdoMet or SAM). This work is a sophisticated tour de force that involves tracer levels of materials, the ultimate stereochemical phenomena, isotope effects, and the exquisite specificity of enzymatic reactions.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Biochemistry

Keywords (Subject):

Chirality / Optical Activity

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Received: August 03, 2009

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