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Glucosamine (Molecule of the Month for January 2014)

Osteoarthritis supplement



Glucosamine is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. A type of glucosamine forms chitin, which composes the exoskeletons of crustaceans and other arthropods, cell walls in fungi and many higher organisms. Glucosamine is one of the most abundant monosaccharides. It is produced commercially by the hydrolysis of crustacean exoskeletons or, less commonly and more expensive to the consumer, by fermentation of a grain such as corn or wheat. Glucosamine is commonly used as a treatment for osteoarthritis, although its acceptance as a medical therapy varies.

Glucosamine was first identified in 1876 by Dr. Georg Ledderhose, but the stereochemistry was not fully defined until 1939 by the work of Walter Haworth. D-Glucosamine is made naturally in the form of glucosamine-6-phosphate, and is the biochemical precursor of all nitrogen-containing sugars. Specifically, glucosamine-6-phosphate is synthesized from fructose-6-phosphate and glutamine as the first step of the hexosamine biosynthesis pathway. The end-product of this pathway is UDP-N-acetylglucosamine (UDP-GlcNAc), which is then used for making glycosaminoglycans, proteoglycans, and glycolipids.

Oral glucosamine is commonly used for the treatment of osteoarthritis. A typical dosage of glucosamine salt is 1,500 mg per day. Since glucosamine is a precursor for glycosaminoglycans, and glycosaminoglycans are a major component of joint cartilage, supplemental glucosamine may help to rebuild cartilage and treat arthritis. Its use as a therapy for osteoarthritis appears safe, but there is conflicting evidence as to its effectiveness. There have been multiple clinical trials of glucosamine as a medical therapy for osteoarthritis, but results have been conflicting. The evidence both for and against glucosamine's efficacy has led to debate among physicians about whether to recommend glucosamine treatment to their patients

Formal Chemical Name (IUPAC)
(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol

References

http://en.wikipedia.org/wiki/Glucosamine

Picture of Glucosamine

click on the picture above to interact
with the 3D model of the
Glucosamine structure
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Picture of Glucosamine

C6 H13 N O5



Update by Karl Harrison
(Molecule of the Month for January 2014 )