Chemical Name: (3 R ,4 S ,5 R )-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
Chemical Formula: C7H10O5
Molecular mass: 174.15 g/mol
Melting Point: 185¨C187 ¡ãC
CAS NO.: 138-59-0
EINECS number: 205-334-2
Shikimic acid is a white crystalline compound of nonnitrogenous acid found in various plants naturally,it is a precursor of many alkaloids, aromatic amino acids, and indole derivatives. It is widely used as a chiral building block for the synthesis of pharmaceuticals.It has effect of anti-inflame, anti- thrombus, easing pain, and also is intermediate of anti-tumor.
Shikimic acid, more commonly known as its anionic form shikimate, is an important biochemical intermediate in plants and microorganisms. Its name comes from the Japanese flower shikimi (¥·¥¥ß,Illicium anisatum), from which it was first isolated and from which it is commercially produced today. Shikimic acid is present in most autotrophic organisms, but the isolation yield is low.
Shikimic acid is a precursor for:
- the aromatic amino acids phenylalanine andtyrosine
- indole, indole derivatives and tryptophan
- many alkaloids and other aromatic metabolites
In pharmaceutical industry, shikimic acid is used as a base material for production of oseltamivir. The low isolation yield of shikimic acid is blamed for the 2005 shortage of oseltamivir.
Hosphoenol pyruvate and erythrose-4-phosphate react to form 3-desoxy-2-keto-arabinoheptonate-7-phosphate.This is then oxidised by NAD¡À to form 3-dehydroquinate.
3-Dehydroquinate is dehydrated to 3-dehydroshikimate, which is reduced by NADPH to shikimate
Shikimate and Chorismate Biosynthesis
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