CHIRAL ALIPHATIC HYDROXY COMPOUNDS IN NATURE: A REVIEW OF BIOLOGICAL FUNCTIONS AND PRACTICAL APPLICATIONS Tomáš MOZGA 1 , Zbyněk PROKOP 2 , Radka CHALOUPKOVÁ 3 and Jiří DAMBORSKÝ 4, * Loschmidt Laboratories, Institute of Experimental Biology and National Centre for Biomolecular Research, Faculty of Science, Masaryk University, Kamenice 5/A4, 625 00 Brno, Czech Republic; e-mail: 1 tomasmozga@chemi.muni.cz, 2 zbynek@chemi.muni.cz, 3 radka@chemi.muni.cz, 4 jiri@chemi.muni.cz Received March 17, 2009 Accepted May 29, 2009 Published online August 26, 2009 Dedicated to Dr. Alfred Bader 1 on the occasion of his 85th birthday to acknowledge his generous support of Czech chemists. Chirality is a phenomenon that pervades the life on the Earth and has a tremendous impor- tance for our daily lives. Many pharmaceuticals, agrochemicals, food additives, pheromones, fragrances and cosmetics are chiral. Chiral compounds play an essential role in biological systems, mainly for chemical communication among living organisms, serving as sex phero- mones, aggregation pheromones, alarm pheromones, trail pheromones, attractants or repel- lent agents. This review summarizes our current knowledge of the biologically relevant chiral aliphatic hydroxy compounds, which are divided into eight classes according to their chemical structure: primary alcohols, secondary alcohols, tertiary alcohols, glycols and diols, hydroxy ketones, hydroxy carboxylic acids, hydroxy carboxylic esters and hydroxy amines. Information on biological functions and practical applications is summarized for each class. This information could be of interest to chemists, biochemists, biologists and pharmacists. A review with 475 references. Ke y w o rd s : Alcohols; Drugs; Pheromones; Odours; Chiral compounds; Hydroxy compounds; Chemical communication; Enantioselective enzymes; Natural products; Chiral pool. The year 2009 offers several important anniversaries to remember and cele- brate. 160 years ago the French scientist Louis Pasteur demonstrated the exis- tence of chiral molecules for the first time 2 . In his early works, he resolved a problem concerning the nature of tartaric acid. This compound derived from living organisms, especially wine lees, rotated the plane of polarized light passing through it, whereas the same compound obtained by chemi- Collect. Czech. Chem. Commun. 2009, Vol. 74, Nos. 7–8, pp. 1195–1278 Chiral Aliphatic Hydroxy Compounds 1195 © 2009 Institute of Organic Chemistry and Biochemistry doi:10.1135/cccc2009038