Standard Article

Chirality in Biology

Biochemistry

  1. Ronald Bentley

Published Online: 15 SEP 2006

DOI: 10.1002/3527600906.mcb.200200008

Reviews in Cell Biology and Molecular Medicine

Reviews in Cell Biology and Molecular Medicine

How to Cite

Bentley, R. 2006. Chirality in Biology. Reviews in Cell Biology and Molecular Medicine. .

Author Information

  1. University of Pittsburgh, Pittsburgh, PA, USA

Publication History

  1. Published Online: 15 SEP 2006

Abstract

An object, structure, or molecule for which the image in a plane mirror cannot be superposed on the original is chiral; for example, the two human hands. Chiral structures or growth forms are common in nature and in manufactured objects. A typical chiral molecule contains a carbon atom linked to four different groups, Cabcd. Such molecules exist in two forms of opposite handedness that are termed enantiomers. Most metabolites are chiral, and enzymes usually exhibit a high degree of specificity toward enantiomers. A molecule containing two chemically like “a” groups, Caabc, is described as prochiral; replacement of one “a” group by “d” leads to a chiral molecule, Cabcd. Enzymes usually discriminate between the two chemically like groups in a prochiral molecule. Enantiomers can have very different physiological actions, for example, taste or odor. With chiral pharmaceutical agents, the enantiomers may also have different physiological actions. Physiological differences arise from the phenomenon of chiral recognition—the ability of biological receptors, enzymes, and some catalysts and reagents to discriminate between the enantiomers of a given compound. Although many hypotheses account for the homochirality observed on planet Earth, the original process or processes leading to this situation remain unclear.

Keywords:

  • Chiral;
  • Chiral Drug;
  • Chiral Methyl;
  • Chiral Phosphorous Atom;
  • Chiral Recognition;
  • Configuration;
  • Diastereoisomer;
  • d/l Notation;
  • Enantiomer;
  • Homochiral;
  • Isomer;
  • Optical Activity;
  • Prochiral (Prostereoisomerism);
  • Racemic;
  • R/S Notation;
  • Stereoisomer