An essential metabolic intermediate with a wide range of uses is shikimic acid. An essential industrial component, shikimic acid serves as a precursor to numerous other chemicals, including oseltamivir phosphate[1].

Shikimate dehydrogenase (SDH) activity was measured by monitoring the reduction of NADP+ at 340 nm and 22°C in the presence of shikimate. The reaction was carried out in 100 mM Tris–HCl buffer (pH 7.0). For determination of apparent steady-state kinetics parameters (Vmax and Km) for the forward reaction (using 3-dehydroshikimate (DHS) and NADPH), the concentration of one substrate was varied (5, 10, 20, 30, 50, 100, and 200 µM) while the other was maintained at a constant saturation level. The reaction was initiated with 6 pmol of homogeneous SD enzyme and monitored for 1 min. Kinetic data were analyzed with double reciprocal plots.[1]
The reverse reaction (oxidation of shikimate) was performed under the same conditions (pH, temperature, substrate concentrations). Activity was measured by following the increase in absorbance at 340 nm due to the NADP+ dependent oxidation of D-shikimate to form NADPH and DHS.[1]

Metabolism / Metabolites
Shikimic acid is metabolized to cyclohexanecarboxylic acid in the gut microbiota, but the aromatization of cyclohexanecarboxylic acid occurs in mammalian tissues. In rats, this acid is primarily metabolized as hippuric acid and excreted in urine, along with 3,4,5,6-tetrahydrohippuric acid and hexahydrohippuric acid, as well as small amounts of benzoyl and cyclohexylcarbonyl glucuronide. In rats, 14C-labeled shikimic acid can be metabolized to hippuric acid and catechols; rat cecal contents can convert it to cyclohexanecarboxylic acid in vitro, and this conversion is almost entirely inhibited by antibiotics.

[1]. Improvement of shikimic acid production in Escherichia coli with growth phase-dependent regulation in the biosynthetic pathway from glycerol. World J Microbiol Biotechnol. 2017 Feb;33(2):25.

Shikimic acid is a cyclohexene carboxylic acid, specifically cyclohexyl-1-en-1-carboxylic acid with hydroxyl groups substituted at positions 3, 4, and 5 (3R, 4S, 5R stereoisomers). It is a metabolic intermediate in plants and microorganisms. It is a metabolite of Escherichia coli, Saccharomyces cerevisiae, and plants. Shikimic acid is a cyclohexene carboxylic acid, a hydroxy monocarboxylic acid, and an α,β-unsaturated monocarboxylic acid. It is the conjugate acid of shikimic acid. Shikimic acid is a metabolite found in or produced by Escherichia coli (K12 strain, MG1655 strain). It has also been reported in Streptomyces niger, Schizocarpus spp., and other organisms with relevant data. Shikimic acid is a metabolite found in or produced by Saccharomyces cerevisiae. It is a trihydroxycyclohexene carboxylic acid metabolite in the shikimic acid pathway. It plays an important role in the biosynthesis of aromatic amino acids, flavonoids, and alkaloids in plants and microorganisms. Shikimic acid (SA) is an important industrial metabolic intermediate and a precursor for the synthesis of oseltamivir phosphate (Tamiflu). It is a key intermediate in the biosynthetic pathway of aromatic amino acids in microorganisms and plants. [1] Shikimic acid can be used to formulate various chemical products, such as aromatic amino acids, indole derivatives, alkaloids and other aromatic metabolites. It can also be used in skin cosmetic preparations, has anti-enzyme activity and can be used as a keratolytic agent. [1] This study proposes a metabolic engineering strategy to increase the yield of shikimic acid in Escherichia coli. To avoid nutritional deficiencies and increase yield, the researchers used a growth-stage-dependent regulation of the aroK gene (encoding shikimic acid kinase I) instead of completely knocking out the gene. [1] In shake-flask culture, the engineered strain SK4/rpsM with growth-stage-dependent aroK expression accumulated 1.28 times more shikimic acid than the control strain SK4/pLac. [1]
Researchers have developed a new pathway that combines heterocodons from Populus trichocarpa to optimize the expression of dehydroquinic acid dehydratase-shikimate dehydrogenase (DHQ-SDH). Using this pathway and the final engineered strain SK5/pSK6 with growth-stage-dependent regulation, a shikimate yield of 5.33 g/L was achieved in shake-flask culture, which is 1.69 times higher than that of the control strain SK5/pSK5. [1]
The kinetic parameters of the purified DHQ-SDH enzyme were determined as follows: In the forward reaction (DHS reduction), the Km value of DHS was 57.9 µM and the Vmax value was 250 U/mg; the Km value of NADPH was 29.7 µM and the Vmax value was 179.5 U/mg. In the reverse reaction (shikimic acid oxidation), the Km value of SA was 81.8 µM and the Vmax value was 16.4 U/mg; the Km value of NADP+ was 27.8 µM and the Vmax value was 20.1 U/mg. [1]

C7H10O5

174.1513

174.052

138-59-0

8742

White to off-white solid powder

1.7±0.1 g/cm3

400.5±45.0 °C at 760 mmHg

185-187 °C(lit.)

210.1±25.2 °C

0.0±2.1 mmHg at 25°C

1.680

-0.92

4

5

1

12

222

3

C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)O

JXOHGGNKMLTUBP-HSUXUTPPSA-N

InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1

(3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

H2O : ~130 mg/mL (~746.48 mM)

Solubility in Formulation 1: 100 mg/mL (574.22 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

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 (Please use freshly prepared in vivo formulations for optimal results.)