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4-Amino-5-aminomethyl-2-methylpyrimidine (CAS 95-02-3)

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Alternate Names:
4-Amino-2-methyl-5-pyrimidinemethanamine; Grewe Diamine
Application:
4-Amino-5-aminomethyl-2-methylpyrimidine is A substrate for the enzyme TenA in the thiamin salvage pathway
CAS Number:
95-02-3
Molecular Weight:
138.17
Molecular Formula:
C6H10N4
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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4-Amino-5-aminomethyl-2-methylpyrimidine is a substrate for the enzyme TenA in the thiamin salvage pathway. 4-Amino-5-aminomethyl-2-methylpyrimidine is a highly functionalized amine compound that has garnered significant attention in scientific research due to its exceptional properties. This versatile reagent exhibits a wide range of applications in chemical synthesis, particularly in the creation of heterocyclic compounds, polymers, and organometallic catalysts. Its diverse utility makes it an invaluable tool for researchers seeking innovative solutions in various fields of study.


4-Amino-5-aminomethyl-2-methylpyrimidine (CAS 95-02-3) References

  1. The nutrition of Staphylococcus aureus. The activities of nicotinamide, aneurin (vitamin B(1)) and related compounds.  |  Knight, BC. 1937. Biochem J. 31: 966-73. PMID: 16746423
  2. Aneurin (vitamin B(1)) and pyruvate metabolism by Staphylococcus aureus.  |  Hills, GM. 1938. Biochem J. 32: 383-91. PMID: 16746631
  3. A new thiamin salvage pathway.  |  Jenkins, AH., et al. 2007. Nat Chem Biol. 3: 492-7. PMID: 17618314
  4. Molecular characterization of the thi3 gene involved in thiamine biosynthesis in Zea mays: cDNA sequence and enzymatic and structural properties of the recombinant bifunctional protein with 4-amino-5-hydroxymethyl-2-methylpyrimidine (phosphate) kinase and thiamine monophosphate synthase activities.  |  Rapala-Kozik, M., et al. 2007. Biochem J. 408: 149-59. PMID: 17696876
  5. Mutagenesis studies on TenA: a thiamin salvage enzyme from Bacillus subtilis.  |  Jenkins, AL., et al. 2008. Bioorg Chem. 36: 29-32. PMID: 18054064
  6. Structural and mutational analysis of TenA protein (HP1287) from the Helicobacter pylori thiamin salvage pathway - evidence of a different substrate specificity.  |  Barison, N., et al. 2009. FEBS J. 276: 6227-35. PMID: 19780837
  7. Salvage of the thiamin pyrimidine moiety by plant TenA proteins lacking an active-site cysteine.  |  Zallot, R., et al. 2014. Biochem J. 463: 145-55. PMID: 25014715
  8. Globally Important Haptophyte Algae Use Exogenous Pyrimidine Compounds More Efficiently than Thiamin.  |  Gutowska, MA., et al. 2017. mBio. 8: PMID: 29018119
  9. A novel thiamine-derived pigment, pyrizepine, formed by the Maillard reaction.  |  Igoshi, A., et al. 2018. Biosci Biotechnol Biochem. 82: 1425-1432. PMID: 29699438
  10. Development of Two Scalable Syntheses of 4-Amino-5-aminomethyl-2-methylpyrimidine: Key Intermediate for Vitamin B1  |  Lei Zhao†‡, Xiao-Dong Ma†, and Fen-Er Chen*†‡. Dev. 2012,. Org. Process Res. 16, 1:, 57–60.
  11. The reaction of 4-Amino-5-aminomethyl-2-methylpyrimidine with amidine salts  |  RF Evans and AV Robertson. 1973. Australian Journal of Chemistry. 26(7): 1599 - 1605.
  12. Stereospecific interactions between tetrakis(.mu.-carboxylato)dirhodium antitumor agents and nucleic acid bases. Crystal structure of the rhodium complex [Rh2(acetato)4(AAMP).3.5H2O] (AAMP = 4-amino-5-(aminomethyl)-2-methylpyrimidine)  |  Katsuyuki Aoki and Hiroshi Yamazaki. 1984,. J. Am. Chem. Soc. 3691–3692: 106, 12,.
  13. Exploring Vitamin B1 Cycling and Its Connections to the Microbial Community in the North Atlantic Ocean  |  Christopher P. Suffridge1*, Luis M. Bolaños1, Kristin Bergauer2,3, Alexandra Z. Worden2,3, Jeff Morré4, Michael J. Behrenfeld5 and Stephen J. Giovannoni1. 2020. Front. Mar. Sci.,. Volume 7 - 2020.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

4-Amino-5-aminomethyl-2-methylpyrimidine, 250 mg

sc-209932A
250 mg
$408.00

4-Amino-5-aminomethyl-2-methylpyrimidine, 2 g

sc-209932
2 g
$1617.00