6001-14-5

Basic information

• Product Name: carboxyaminoimidazole ribotide
• Synonyms: carboxyaminoimidazole ribotide;1-(5-O-Phosphono-β-D-ribofuranosyl)-5-amino-1H-imidazole-4-carboxylic acid;5-Aminoimidazole-4-carboxylic acid ribonucleotide;5'-Phosphoribosyl-5-aminoimidazole-4-carboxylic acid;CAIR;Carboxy-AIR;1H-IMidazole-4-carboxylicacid, 5-aMino-1-(5-O-phosphono-b-D-ribofuranosyl)
• CAS NO: 6001-14-5
• Molecular Formula: C₉H₁₄N₃O₉P
• Molecular Weight: 339.2
• Mol File: 6001-14-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 865.9±75.0 °C(Predicted)
• Appearance: /
• Density: 2.30±0.1 g/cm3(Predicted)
• PKA: 1.86±0.10(Predicted)
• CAS DataBase Reference: carboxyaminoimidazole ribotide(CAS DataBase Reference)
• NIST Chemistry Reference: carboxyaminoimidazole ribotide(6001-14-5)
• EPA Substance Registry System: carboxyaminoimidazole ribotide(6001-14-5)

Safety Data

• Hazardous Substances Data: 6001-14-5(Hazardous Substances Data)

Usage

Description

Carboxyaminoimidazole ribotide (Carboxy-AIR) is an intermediate compound in the histidine biosynthesis pathway. It plays a crucial role in the production of histidine, an essential amino acid for various biological processes.

Uses

Used in Pharmaceutical Industry:
Carboxy-AIR is used as an inhibitor for the treatment of melanoma, a type of skin cancer. By inhibiting the enzymes involved in the histidine biosynthesis pathway, it can potentially disrupt the growth and proliferation of melanoma cells.
Used in Biochemical Research:
Carboxy-AIR is used as a substrate in the study of histidine biosynthesis and related metabolic pathways. It helps researchers understand the mechanisms and regulation of histidine production in cells.
Used in Industrial Fermentation:
Carboxy-AIR can be used in the production of ethanol through microbial fermentation. By optimizing the histidine biosynthesis pathway, it can enhance the efficiency of ethanol production, which is an important biofuel and industrial chemical.

Synthetic route

N1-(5-O-phospho-β-D-ribofuranosyl)-4-(ethoxycarbonyl)-5-aminoimidazole (51172-80-6) → 5-amino-4-carboxylic acid-1H-imidazol-1-yl ribotide (6001-14-5)

Conditions	Yield
With sodium hydroxide In water at 80℃; for 2h;

5-amino-1-5-phosphono-β-D-ribofuranosyl>-1H-imidazole + KHCO3 → 5-amino-4-carboxylic acid-1H-imidazol-1-yl ribotide (6001-14-5)

Conditions	Yield
With enzymeextracts from poultry liver

N1-(5-O-phospho-2,3-O-isopropylidene-β-D-ribofuranosyl)-4-(ethoxycarbonyl)-5-aminoimidazole (57204-10-1) → 5-amino-4-carboxylic acid-1H-imidazol-1-yl ribotide (6001-14-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / Dowex 50 x 4 (H+ form) / methanol; H2O / 5 h / 20 °C 2: 0.2M NaOH / H2O / 2 h / 80 °C View Scheme

N1-(2',3'-O-isopropylidene-β-D-ribofuranosyl)-4-ethoxycarbonyl-5-aminoimidazole (37668-83-0) → 5-amino-4-carboxylic acid-1H-imidazol-1-yl ribotide (6001-14-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 0.72 g / 1.) POCl3, pyridine, H2O, 2.) NaOH solution / acetonitrile / 3.5 h / 0 °C 2: 94 percent / Dowex 50 x 4 (H+ form) / methanol; H2O / 5 h / 20 °C 3: 0.2M NaOH / H2O / 2 h / 80 °C View Scheme

L-Aspartic acid (56-84-8) + 5-amino-4-carboxylic acid-1H-imidazol-1-yl ribotide (6001-14-5) → N-[5-amino-1-(O5-phosphono-β-D-ribofuranosyl)-1H-imidazole-4-carbonyl]-L-aspartic acid (3031-95-6)

Conditions	Yield
With enzymeextracts from chicken liver; ATP

5-amino-4-carboxylic acid-1H-imidazol-1-yl ribotide (6001-14-5) → N1-(β-D-ribofuranosyl)-5-carboxy-5-aminoimidazole (6001-15-6)

Conditions	Yield
With rAPid alkaline phosphatase at 37℃; for 0.25h; Enzymatic reaction;

Upstream product

• 51172-80-6 N¹-(5-O-phospho-β-D-ribofuranosyl)-4-(ethoxycarbonyl)-5-aminoimidazole 
• 57204-10-1 N¹-(5-O-phospho-2,3-O-isopropylidene-β-D-ribofuranosyl)-4-(ethoxycarbonyl)-5-aminoimidazole 
• 37668-83-0 N¹-(2',3'-O-isopropylidene-β-D-ribofuranosyl)-4-ethoxycarbonyl-5-aminoimidazole 

Downstream Products

• 3031-95-6 (5-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((phosphonooxy)methyl)tetrahydrofuran-2-yl)-1H-imidazole-4-carbonyl)-L-aspartic acid 

Relevant articles and documents

ANALOGS OF 4-CARBOXY-5-AMINOIMIDAZOLE RIBOTIDE (CAIR) WITH A MODIFIED PHOSPHORIC ACID RESIDUE

-