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MedKoo Cat#: 462998 | Name: Aminoimidazole ribotide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Aminoimidazole ribotide
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: 295.0569

Molecular Weight: 295.19

Elemental Analysis: C, 32.55; H, 4.78; N, 14.24; O, 37.94; P, 10.49

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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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

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
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.