Aminoshikimic acid is a synthetic crystalline carboxylic acid

Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of at least one carboxyl group. The general formula of a carboxylic acid is R-COOH, where R is some monovalent functional group...

. It is characterized by multiple stereogenic centers and functional groups arrayed around a six-membered carbocyclic ring. Aminoshikimic acid is also an alternative to shikimic acid

Shikimic acid

Shikimic acid, more commonly known as its anionic form shikimate, is an important biochemical metabolite in plants and microorganisms. Its name comes from the Japanese flower shikimi , from which it was first isolated....

 as a starting material for the synthesis of neuraminidase inhibitors such as the antiinfluenza agent oseltamivir

Oseltamivir

Oseltamivir INN , an antiviral drug, slows the spread of influenza virus between cells in the body by stopping the virus from chemically cutting ties with its host cell; median time to symptom alleviation is reduced by 0.5–1 day. The drug is sold under the trade name Tamiflu, and is taken orally...

 (Tamiflu).

History

Aminoshikimic acid is an unnatural carbohydrate, although aminoshikimic acid is the namesake of the aminoshikimate pathway

Aminoshikimate pathway

Aminoshikimate pathway is a novel variation of the shikimate pathway. The aminoshikimate pathway was first discovered and studied in rifamycin B producer Amycolatopsis mediterranei...

, which generates the 3-amino-5-hydroxybenzoic acid (AHBA) starter unit required for the biosynthesis of the ansamycin

Ansamycin

Ansamycins is a family of secondary metabolites that show antimicrobial activity against many gram-positive and some gram-negative bacteria and includes various compounds, among which: streptovaricins and rifamycins...

s and mitomycin

Mitomycin

The mitomycins are a family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae. One of these compounds, mitomycin C, finds use as a chemotherapeutic agent by virtue of its antitumour antibiotic activity. It is given intravenously to treat...

s. The first microbe-catalyzed syntheses of aminoshikimic acid were described by Guo and Frost in 2004.

Pharmaceutical uses

Aminoshikimic acid is an intriguing alternative to shikimic acid as a starting material for the synthesis of neuraminidase inhibitors such as the antiinfluenza agent oseltamivir. Aminoshikimic acid is also a versatile chiral starting material for the synthesis of new pharmaceuticals. As with shikimic acid, aminoshikimic acid is an attractive candidate for use as the core scaffold for synthesis of combinatorial libraries.