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Chemical Reaction: The Chirality of Life

By: Steve Herman
Posted: October 14, 2008, from the May 2006 issue of GCI Magazine.

page 3 of 4

The cosmetic industry has been customizing proteins for many years. Hydrolyzed proteins, quaternized proteins, protein fragments and proteins with pendant groups added to the reactive sites of amino acids are common. These products usually are modified for solubility or substantivity, not biological activity. The main exception is the short peptide chains used in skin care. New proteins using genetic engineering, and incorporating the proper chiral forms would, potentially, be a giant evolutionary step in raw material construction.

Making designer proteins from scratch is well beyond current technology, and even predicting the behavior of a completely new molecule would overwhelm available computational methods. New proteins are being made from existing structures, retaining the desirable traits of the original in addition to the properties contributed by the specially engineered amino acid.

Pharmaceuticals are 70% of a $15 billion chiral chemical market.2 It surely will become an increasingly important factor in skin care. Using naturally derived materials will usually provide the right stereochemistry, but as technology advances, there will be increased likelihood of chiral factors impacting either raw material synthesis or biological activity.

Companies that commercialize chiral chemicals have specific challenges relating to synthesis, catalysis and separation by methods such as chiral liquid chromatography. Technology ranges from the newest biocatalytic transformations to the protecting groups that aid asymmetric synthesis. To create new enantioselective technology, researchers use the chiral pool, resolution of racemates, and asymmetric synthesis. The chiral pool consists of all the carbohydrates, amino acids, lipids, terpenes and alkaloids from plant and animal sources. Either chemical or biocatalytic methods are used.

A highly unscientific survey at a recent meeting of the New York Society of Cosmetic Chemists revealed little awareness of the potential for developing a new generation of cosmetic actives based on chiral properties. Yet, in the past, the cosmetic industry has taken many concepts from pharmaceuticals. If history repeats itself, and it often does, chirality will someday be one more tool in the quest for the perfect cosmetic.