Shikimic Acid

Catalog Number: S001
Chemical Name: (3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
Botanical Source: Illicium Lanceolatum A.C. Smith
Empirical Formula: C7H10O5
Formula Weight: 174.15
CAS Number: 138-59-0
Purity: 98% determined by HPLC
Appearance: White powder
Melting Temperature: 185–187°C
Storage Temperature: Room temperature
Solubility: 50 mg/mL in water
22.5 mg/mL in ethanol
0.15mg/mL in ether
Other Features: Light sensitive
Price:

Pharmacological Actions: Shikimic acid is the key compound of the common aromatic amino acid pathway (Shikimic acid pathway) that is essential for algae, higher plants, bacteria, fungi, and parasite, but absent in mammals (1-3). Therefore this pathway is an important target for the development of nontoxic antimicrobial agents (4), herbicides (5), and antiparasite drugs (6), such as anti-M. tuberculosis
agents (7-9). Shikimic acid is also a key starting material for the synthesis of the neuramidase inhibitor GS4104 for the treatment of antiviral infections (7).

References:

1.       Oberts F, Roberts CW, Johnson JJ, Kyle DE, Krell T, Coggins JR, Coombs GH, Milhous WK, Tzipori S, Ferguson DJP, Chakrabarti D, McLeod R (1998) Evidence for the Shikimate Pathway in Apicomplexan Parasites. Nature 393, 801-805.

2.        Haslam E (1993) Shikimic Acid: Metabolism and Metabolites. John Wiley & Sons, Chichester.

3.        Kishore GM, and Shah DM (1988) Amino Acid Biosynthesis Inhibitors as Herbicides. Annu Rev Biochem 57, 627-663.

4.        Davies GM, Barrett-Bee KJ, Jude DA, Lehan M, Nichols WW, Pinder PE, Thain JL, Watkins WJ, and Wilson RG (1994) (6S)-6-fluoroshikimic Acid, An Antibacterial Agent Acting on the Aromatic Biosynthetic Pathway. Antimicrob Agents Chemother 38, 403-406.

5.        Coggins JR (1989) The Shikimate Pathway as A Target for Herbicides, in Herbicides and Plant Metabolism. (Dodge, A., Ed.) p 97-112, Cambridge University Press, Cambridge, U.K.

6.        Ridley RG (1998) Planting New Targets for Antiparasitic Drugs. Nat Med 4, 894-895.

7.        Krämer M, Bongaerts J, Bovenberg R, Kremer S, Müller U, Orf S, Wubbolts M and Raeven L (2003) Metabolic Engineering for Microbial Production of Shikimic Acid. Metabolic Engineering 5, 277-283.

8.        Zhang X, Zhang S, Hao F, Lai X, Yu H, Huang Y and Wang H (2005) Expression, Purification and Properties of Shikimate Dehydrogenase from Mycobacterium Tuberculosis. J Biochem Mol Biol 38, 624-631.

9.        Gan J, Gu Y, Li Y, Yan H and Ji X (2006) Crystal Structure of Mycobacterium tuberculosis Shikimate Kinase in Complex with Shikimic Acid and An ATP Analogue. Biochemistry 45, 8539-8545.