Aminoimidazole ribotide

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MedKoo CAT#: 462998

CAS#: 25635-88-5 (free acid)

Description: Aminoimidazole ribotide is a biochemical intermediate in the formation of purine nucleotides via inosine-5-monophosphate, and hence is a building block for DNA and RNA. The vitamins thiamine and cobalamin also contain fragments derived from AIR. It is an intermediate in the adenine pathway and is synthesized from 5′-phosphoribosylformylglycinamidine by AIR synthetase.


Chemical Structure

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Aminoimidazole ribotide
CAS# 25635-88-5 (free acid)

Theoretical Analysis

MedKoo Cat#: 462998
Name: Aminoimidazole ribotide
CAS#: 25635-88-5 (free acid)
Chemical Formula: C8H14N3O7P
Exact Mass: 295.06
Molecular Weight: 295.188
Elemental Analysis: C, 32.55; H, 4.78; N, 14.24; O, 37.94; P, 10.49

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 127646-03-1 (lithium)   25635-88-5 (free acid)    

Synonym: 5-Aminoimidazole ribotide; 5-Amino-4-imidazole ribotide; 5-Aminoimidazole ribotide; AIR (nucleotide);

IUPAC/Chemical Name: ((2R,3S,4R,5R)-5-(5-amino-1H-imidazol-1-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate

InChi Key: PDACUKOKVHBVHJ-XVFCMESISA-N

InChi Code: InChI=1S/C8H14N3O7P/c9-5-1-10-3-11(5)8-7(13)6(12)4(18-8)2-17-19(14,15)16/h1,3-4,6-8,12-13H,2,9H2,(H2,14,15,16)/t4-,6-,7-,8-/m1/s1

SMILES Code: Nc1n([C@@H]2O[C@@H]([C@H]([C@H]2O)O)COP(O)(O)=O)cnc1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 295.19 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Pelet A, Skopova V, Steuerwald U, Baresova V, Zarhrate M, Plaza JM, Hnizda A, Krijt M, Souckova O, Wibrand F, Andorsdóttir G, Joensen F, Sedlak D, Bleyer AJ, Kmoch S, Lyonnet S, Zikanova M. PAICS deficiency, a new defect of de novo purine synthesis resulting in multiple congenital anomalies and fatal outcome. Hum Mol Genet. 2019 Nov 15;28(22):3805-3814. doi: 10.1093/hmg/ddz237. PMID: 31600779.

2: Streeter CC, Lin Q, Firestine SM. Isatins Inhibit N5-CAIR Synthetase by a Substrate Depletion Mechanism. Biochemistry. 2019 Apr 30;58(17):2260-2268. doi: 10.1021/acs.biochem.8b00939. Epub 2019 Apr 17. PMID: 30964980; PMCID: PMC7018488.

3: Gagnon DM, Stich TA, Mehta AP, Abdelwahed SH, Begley TP, Britt RD. An Aminoimidazole Radical Intermediate in the Anaerobic Biosynthesis of the 5,6-Dimethylbenzimidazole Ligand to Vitamin B12. J Am Chem Soc. 2018 Oct 10;140(40):12798-12807. doi: 10.1021/jacs.8b05686. Epub 2018 Sep 27. PMID: 30208703; PMCID: PMC6435355.

4: Kijima Y, Hayashi M, Yamada K, Tazuya-Murayama K. The Biosynthesis of the Pyrimidine Moiety of Thiamin in Halobacterium salinarum. J Nutr Sci Vitaminol (Tokyo). 2016;62(2):130-3. doi: 10.3177/jnsv.62.130. PMID: 27264098.

5: Mehta AP, Abdelwahed SH, Fenwick MK, Hazra AB, Taga ME, Zhang Y, Ealick SE, Begley TP. Anaerobic 5-Hydroxybenzimidazole Formation from Aminoimidazole Ribotide: An Unanticipated Intersection of Thiamin and Vitamin B₁₂ Biosynthesis. J Am Chem Soc. 2015 Aug 26;137(33):10444-7. doi: 10.1021/jacs.5b03576. Epub 2015 Aug 13. PMID: 26237670; PMCID: PMC4753784.

6: Bazurto JV, Heitman NJ, Downs DM. Aminoimidazole Carboxamide Ribotide Exerts Opposing Effects on Thiamine Synthesis in Salmonella enterica. J Bacteriol. 2015 Sep;197(17):2821-30. doi: 10.1128/JB.00282-15. Epub 2015 Jun 22. PMID: 26100042; PMCID: PMC4524041.

7: Stoyanov A, Petrova P, Lyutskanova D, Lahtchev K. Structural and functional analysis of PUR2,5 gene encoding bifunctional enzyme of de novo purine biosynthesis in Ogataea (Hansenula) polymorpha CBS 4732T. Microbiol Res. 2014 May-Jun;169(5-6):378-87. doi: 10.1016/j.micres.2013.08.008. Epub 2013 Sep 25. PMID: 24135445.

8: Palmer LD, Downs DM. The thiamine biosynthetic enzyme ThiC catalyzes multiple turnovers and is inhibited by S-adenosylmethionine (AdoMet) metabolites. J Biol Chem. 2013 Oct 18;288(42):30693-9. doi: 10.1074/jbc.M113.500280. Epub 2013 Sep 6. PMID: 24014032; PMCID: PMC3798539.

9: Palmer LD, Dougherty MJ, Downs DM. Analysis of ThiC variants in the context of the metabolic network of Salmonella enterica. J Bacteriol. 2012 Nov;194(22):6088-95. doi: 10.1128/JB.01361-12. Epub 2012 Sep 7. PMID: 22961850; PMCID: PMC3486400.

10: Jurgenson CT, Ealick SE, Begley TP. Biosynthesis of Thiamin Pyrophosphate. EcoSal Plus. 2009 Aug;3(2):10.1128/ecosalplus.3.6.3.7. doi: 10.1128/ecosalplus.3.6.3.7. PMID: 26443755; PMCID: PMC6039189.

11: Martinez-Gomez NC, Downs DM. ThiC is an [Fe-S] cluster protein that requires AdoMet to generate the 4-amino-5-hydroxymethyl-2-methylpyrimidine moiety in thiamin synthesis. Biochemistry. 2008 Sep 2;47(35):9054-6. doi: 10.1021/bi8010253. Epub 2008 Aug 8. PMID: 18686975; PMCID: PMC2538623.

12: Dougherty MJ, Downs DM. A connection between iron-sulfur cluster metabolism and the biosynthesis of 4-amino-5-hydroxymethyl-2-methylpyrimidine pyrophosphate in Salmonella enterica. Microbiology (Reading). 2006 Aug;152(Pt 8):2345-2353. doi: 10.1099/mic.0.28926-0. PMID: 16849799.

13: Lawhorn BG, Mehl RA, Begley TP. Biosynthesis of the thiamin pyrimidine: the reconstitution of a remarkable rearrangement reaction. Org Biomol Chem. 2004 Sep 7;2(17):2538-46. doi: 10.1039/B405429F. Epub 2004 Aug 11. PMID: 15326535.

14: Dougherty MJ, Downs DM. A mutant allele of rpoD results in increased conversion of aminoimidazole ribotide to hydroxymethyl pyrimidine in Salmonella enterica. J Bacteriol. 2004 Jun;186(12):4034-7. doi: 10.1128/JB.186.12.4034-4037.2004. PMID: 15175319; PMCID: PMC419934.

15: Ramos I, Downs DM. Anthranilate synthase can generate sufficient phosphoribosyl amine for thiamine synthesis in Salmonella enterica. J Bacteriol. 2003 Sep;185(17):5125-32. doi: 10.1128/jb.185.17.5125-5132.2003. PMID: 12923085; PMCID: PMC180985.

16: Dougherty M, Downs DM. The stm4066 gene product of Salmonella enterica serovar Typhimurium has aminoimidazole riboside (AIRs) kinase activity and allows AIRs to satisfy the thiamine requirement of pur mutant strains. J Bacteriol. 2003 Jan;185(1):332-9. doi: 10.1128/jb.185.1.332-339.2003. PMID: 12486071; PMCID: PMC141821.

17: Allen S, Zilles JL, Downs DM. Metabolic flux in both the purine mononucleotide and histidine biosynthetic pathways can influence synthesis of the hydroxymethyl pyrimidine moiety of thiamine in Salmonella enterica. J Bacteriol. 2002 Nov;184(22):6130-7. doi: 10.1128/jb.184.22.6130-6137.2002. PMID: 12399482; PMCID: PMC151968.

18: Amara RR, Shanti S, Satchidanandam V. Characterization of novel immunodominant antigens of Mycobacterium tuberculosis. Microbiology (Reading). 1998 May;144 ( Pt 5):1197-203. doi: 10.1099/00221287-144-5-1197. PMID: 9611794.

19: Firestine SM, Misialek S, Toffaletti DL, Klem TJ, Perfect JR, Davisson VJ. Biochemical role of the Cryptococcus neoformans ADE2 protein in fungal de novo purine biosynthesis. Arch Biochem Biophys. 1998 Mar 1;351(1):123-34. doi: 10.1006/abbi.1997.0512. PMID: 9500840.

20: Beck BJ, Downs DM. The apbE gene encodes a lipoprotein involved in thiamine synthesis in Salmonella typhimurium. J Bacteriol. 1998 Feb;180(4):885-91. doi: 10.1128/JB.180.4.885-891.1998. PMID: 9473043; PMCID: PMC106968.