Galactose (, galacto- + -ose, sometimes abbreviated gal) is a common monosaccharide, i.e. a simple sugar. It is classified as a reducing hexose, more specifically an aldohexose. In terms of structure, it is a C-4 epimer of glucose. A white, water-soluble solid, it is about 80–90% as sweet as glucose and about 65% as sweet as sucrose.
Occurrence Galactan is a polymeric form of galactose found in hemicellulose, and forming the core of the galactans, a class of natural polymeric carbohydrates. D-Galactose is also known as brain sugar since it is a component of glycoproteins (oligosaccharide-protein compounds) found in nerve tissue. Galactofuranose occurs in bacteria, fungi and protozoa, and is recognized by a putative chordate immune lectin intelectin through its exocyclic 1,2-diol.
Relationship to lactose Galactose, when combined with glucose (another monosaccharide) through a condensation reaction, gives the disaccharide called lactose. The hydrolysis of lactose to glucose and galactose is catalyzed by the enzymes lactase and β-galactosidase. The latter is produced by the lac operon in Escherichia coli. In nature, lactose is found primarily in milk and milk products. Consequently, various food products made with dairy-derived ingredients can contain lactose. Galactose is metabolised to glucose by the three principal enzymes in a mechanism known as the Leloir pathway. The enzymes are listed in the order of the metabolic pathway: galactokinase (GALK), galactose-1-phosphate uridyltransferase (GALT), and UDP-galactose 4′-epimerase (GALE). In human lactation, galactose is required in a 1 to 1 ratio with glucose to enable the mammary glands to synthesize and secrete lactose. In a study where women were fed a diet containing galactose, 69 ± 6% of glucose and 54 ± 4% of galactose in the lactose they produced were derived directly from plasma glucose, while 7 ± 2% of the glucose and 12 ± 2% of the galactose in the lactose, were derived directly from plasma galactose. 25 ± 8% of the glucose and 35 ± 6% of the galactose was synthesized from smaller molecules in a process referred to in the paper as hexoneogenesis. This suggests that the synthesis of galactose is supplemented by direct uptake and the use of plasma galactose when present.
Structure and isomerism
Galactose exists in both open-chain and cyclic form. The open-chain form is an aldehyde (RCHO). Four isomers are cyclic, two of them with a pyranose (six-membered) ring and two with a furanose (five-membered) ring. Each cyclic form can exist as two anomers, named alpha and beta, since a new stereocenter is generated upon cyclization at the site of the carbonyl. In the pyranose form, the OH group on C-3 is axial.
Metabolism
Glucose is more stable than galactose and is less susceptible to the formation of nonspecific glycoconjugates, molecules with at least one sugar attached to a protein or lipid. Many speculate that it is for this reason that a pathway for rapid conversion from galactose to glucose has been highly conserved among many species. The main pathway of galactose metabolism is the Leloir pathway; humans and other species, however, have been noted to contain several alternate pathways, such as the De Ley Doudoroff Pathway. The Leloir pathway consists of the latter stage of a two-part process that converts β-D-galactose to UDP-glucose. The initial stage is the conversion of β-D-galactose to α-D-galactose by the enzyme, mutarotase (GALM). The Leloir pathway then carries out the conversion of α-D-galactose to UDP-glucose via three principal enzymes: Galactokinase (GALK) phosphorylates α-D-galactose to galactose-1-phosphate, or Gal-1-P; Galactose-1-phosphate uridyltransferase (GALT) transfers a UMP group from UDP-glucose to Gal-1-P to form UDP-galactose; and finally, UDP galactose-4'-epimerase (GALE) interconverts UDP-galactose and UDP-glucose, thereby completing the pathway. The above mechanisms for galactose metabolism are necessary because the human body cannot directly use galactose for energy metabolism, and it must first go through one of these processes. Galactosemia is an inability to properly break down galactose due to a genetically inherited mutation in one of the enzymes in the Leloir pathway. As a result, the consumption of even small quantities is harmful to galactosemics.
Sources Galactose is found in dairy products, avocados, sugar beets, other gums and mucilages. It is also synthesized by the body, where it forms part of glycolipids and glycoproteins in several tissues; and is a by-product from the third-generation ethanol production process (from macroalgae).
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