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Novel Aminomethanesulfonate Buffers for Biological Buffering in the Acidic Range *

Novel Aminomethanesulfonate Buffers for Biological Buffering in the Acidic Range *. Robert D. Long, Newton P. Hilliard Jr., Daniel Dei, Enoch A. Mensah. Paper # 432. * Patent pending. Goal. New buffers for biological systems at pH levels well into acidic range (below pH 5.5)

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Novel Aminomethanesulfonate Buffers for Biological Buffering in the Acidic Range *

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  1. Novel Aminomethanesulfonate Buffers for Biological Buffering in the Acidic Range* Robert D. Long, Newton P. Hilliard Jr., Daniel Dei, Enoch A. Mensah Paper # 432 * Patent pending

  2. Goal New buffers for biological systems at pH levels well into acidic range (below pH 5.5) • Needed for acidophilic bacteria studies • Enzyme/biotech systems at acidic pH • “Good” buffers limited usability below physiological range • Metabolic interferences from citrate, borate, phosphate, and other systems

  3. “Good” Buffers • Tertiary or secondary amines with alkylsulfonic acid attached (varying alkyl chain length) Ref: Good, N. E., et al. Biochemistry1966, 5(2), 467-477. Good, N. E., and Izawa, S. Methods Enzymol.1980, 24, 53-68.

  4. Desirable Properties (per N. Good) • midrange pKa • maximum water solubility and minimum solubility in all other solvents • minimal salt effects • minimal change in pKa with temperature • chemically and enzymatically stable • minimal absorption in visible or UV spectral range and • reasonably easily synthesized.

  5. Some Lower pH Good Buffers

  6. Target Compounds

  7. Routes to Current Good Buffers

  8. Synthesis of Aminomethanesulfonates Ref: Johnson, T.B. JACS 1941, 63, 1571-1572. Raschig, F.; Prahl, W., Ann.1926, 448, 265. Gilbert, E. E., Sulfonation and Related Reactions; Interscience; NY, 1965 Ref: Knoevenagel, E., Ber. 1904, 37, 4087. Neelakantan & Hartung, JOC1959, 24, 1943.

  9. Synthesis of Other Targets

  10. Ionization of Aminoalkylsulfonates MMS – morpholinomethanesulfonic acid

  11. Crystallography of MMS Sodium salt form (no protonation)

  12. Crystallography of HEPMS Note: Zwitterion Protonated amine Sulfonate anion

  13. pKa Comparison * pKa2 value

  14. Initial Growth Studies E. coli strain HB101 at pH 7.2 and 37ºC for 18 hours

  15. In-progress Biological Testing • Halothiobacillus neapolitanus at acidic pH • E. coli & H. neapolitanus transformation efficiency • Enzyme reactions (food technology/ glycosidases) in the acidic range Preliminary testing shows increased efficiency/activity in all three areas with MMS

  16. Acknowledgements • BRIN/INBRe (NIH-NCRR P20-016840) (Infrastructure grant) • Dr. Newton Hilliard (Biochemistry) • Grad students • Enoch Mensah • Daniel Dei • Science & Technology Corp. (STC) at Univ. of New Mexico (Patent pending) (For more info contact robert.long@enmu.edu or ssheehan@unm.edu)

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