143393-03-7

Basic information

• Product Name: S-3-P TrisodiuM
• Synonyms: (3R,4S,5R)-4,5-Dihydroxy-3-(phosphonooxy)-1-cyclohexene-1-carboxylic Acid SodiuM Salt;[3R-(3α,4α,5β)]-4,5-Dihydroxy-3-(phosphonooxy)-1- cyclohexene-1-carboxylic Acid TrisodiuM Salt;S-3-P TrisodiuM;ShikiMate-3-phosphate TrisodiuM Salt 90%;ShikiMate-3-phosphate TrisodiuM Salt (90%);Shikimate-3-phosphate (sodium salt)
• CAS NO: 143393-03-7
• Molecular Formula: C₇H₈O₈P*3Na
• Molecular Weight: 320.076691
• Product Categories: Chiral Reagents;Phosphorylating and Phosphitylating Agents
• Mol File: 143393-03-7.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C
• Solubility: Methanol (Slightly), Water (Slightly, Sonicated)
• Stability: Very Hygroscopic
• CAS DataBase Reference: S-3-P TrisodiuM(CAS DataBase Reference)
• NIST Chemistry Reference: S-3-P TrisodiuM(143393-03-7)
• EPA Substance Registry System: S-3-P TrisodiuM(143393-03-7)

Safety Data

• Hazardous Substances Data: 143393-03-7(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
S-3-P TrisodiuM is used as a target for the broad-spectrum herbicide N-(phosphonomethyl)glycine (glyphosate). Glyphosate inhibits the enzyme EPSPS, which is essential for the synthesis of aromatic amino acids in plants, leading to their death. This application is crucial in controlling various types of weeds in agricultural fields.
Used in Pharmaceutical Industry:
S-3-P TrisodiuM is used as a starting material for the synthesis of various pharmaceutical compounds, particularly those related to the shikimate pathway. The shikimate pathway is involved in the production of essential aromatic amino acids and other secondary metabolites, which are vital for the development of new drugs and therapies.
Used in Research and Development:
S-3-P TrisodiuM is used as a research tool in the study of the shikimate pathway and its role in the biosynthesis of aromatic amino acids. Understanding the pathway's mechanisms and regulation can lead to the development of novel strategies for the control of plant growth, the production of bioactive compounds, and the design of new herbicides and pharmaceuticals.
Used in Biotechnology:
S-3-P TrisodiuM is used in biotechnological applications, such as the engineering of microorganisms to produce aromatic amino acids and other valuable compounds. By modifying the expression of genes involved in the shikimate pathway, scientists can enhance the production of these compounds, which can be used in various industries, including pharmaceuticals, agriculture, and the food industry.

Upstream product

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• 143308-76-3 Methyl 4,5-O-diacetyl-3-O-(dimethoxytrityl)-(-)-shikimate 
• 143308-75-2 Methyl 5-O-acetyl-3-O-(dimethoxytrityl)-(-)-shikimate 
• 143308-78-5 Methyl 4,5-O-diacetyl-(-)-shikimate dibenzyl 3-phosphate 
• 143308-77-4 Methyl 4,5-O-diacetyl-(-)-shikimate 
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• 88165-26-8 methyl 3,4-O-isopropylideneshikimate 
• 282535-09-5 (2S,3S,4aR,6R,8R,8aS)-8-(Bis-benzyloxy-phosphoryloxy)-6-hydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 245054-32-4 methyl (3R,4S,5R)-3-hydroxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate 
• 176798-26-8 (2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 40983-58-2 methyl shikimate 
• 282535-08-4 (2S,3S,4aR,8R,8aS)-8-(Bis-benzyloxy-phosphoryloxy)-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 1053643-69-8 Methyl 4,5-O-diacetyl-(-)-shikimate 3-phosphate 
• 138-59-0 shikimic acid 

Relevant articles and documents

Efficient syntheses-of (-)-shikimate and (-)-quinate 3-phosphate via trans vicinal diol protection with 2,2,3,3-tetramethoxybutane (TMB) of shikimic and quinic acids

(-)-Shikimate 3-phosphate and (-)-quinate 3-phosphate can be synthesized by selective protection of their trans diol functionality using 2,2,3,3- tetramethoxybutane (TMB) using D-(-)-shikimic acid and D-(-)-quinic acid as starting materials. This versatile reagent facilitates the synthesis of these important biological targets in fewer steps than previously reported. By the proper choice of protecting group for C-3 hydroxyl in D-(-)-quinic acid, it can be converted to a key intermediate in the synthesis of (-)-shikimate 3- phosphate. (C) 2000 Elsevier Science Ltd.

Solution Conformations of Two Shikimate 3-Phosphates: Determination by NMR and Molecular Mechanics Calculations

The solution conformation of two substituted cyclohexenes: shikimate 3-phosphate (S3P), 1, and a conformationally constrained derivative, the pyruvoyl ketal of 4,5-shikimate 3-phosphate (EPSP ketal), 2, have been determined by a combination of NMR and mol