Stephen C Miller

Summary

Affiliation: University of Massachusetts Medical School
Country: USA

Publications

  1. doi request reprint Reductively-labile sulfonate ester protecting groups that are rapidly cleaved by physiological glutathione
    Adam Choi
    Department of Biochemistry and Molecular Pharmacology, University of Massachusetts Medical School, 364 Plantation St, Worcester, MA 01605, USA
    Org Biomol Chem . 2017
  2. pmc Profiling sulfonate ester stability: identification of complementary protecting groups for sulfonates
    Stephen C Miller
    Department of Biochemistry and Molecular Pharmacology, University of Massachusetts Medical School, 364 Plantation St, Worcester, Massachusetts 01605, USA
    J Org Chem 75:4632-5. 2010
  3. pmc Synthesis of near-IR fluorescent oxazine dyes with esterase-labile sulfonate esters
    Steven M Pauff
    Department of Biochemistry and Molecular Pharmacology, University of Massachusetts Medical School, Worcester, Massachusetts 01655, USA
    Org Lett 13:6196-9. 2011
  4. pmc A trifluoroacetic acid-labile sulfonate protecting group and its use in the synthesis of a near-IR fluorophore
    Steven M Pauff
    Department of Biochemistry and Molecular Pharmacology, University of Massachusetts Medical School, 364 Plantation Street, Worcester, Massachusetts 01605, USA
    J Org Chem 78:711-6. 2013
  5. doi request reprint Design and application of esterase-labile sulfonate protecting groups
    Laert Rusha
    Department of Biochemistry and Molecular Pharmacology, University of Massachusetts Medical School, 364 Plantation St, Worcester, MA 01605, USA
    Chem Commun (Camb) 47:2038-40. 2011

Collaborators

  • Steven M Pauff
  • Adam Choi
  • Laert Rusha

Detail Information

Publications5

  1. doi request reprint Reductively-labile sulfonate ester protecting groups that are rapidly cleaved by physiological glutathione
    Adam Choi
    Department of Biochemistry and Molecular Pharmacology, University of Massachusetts Medical School, 364 Plantation St, Worcester, MA 01605, USA
    Org Biomol Chem . 2017
    ..Self-immolative cleavage releases the sulfonate and the two-electron reduction product of a thioquinone methide...
  2. pmc Profiling sulfonate ester stability: identification of complementary protecting groups for sulfonates
    Stephen C Miller
    Department of Biochemistry and Molecular Pharmacology, University of Massachusetts Medical School, 364 Plantation St, Worcester, Massachusetts 01605, USA
    J Org Chem 75:4632-5. 2010
    ..This work compares the intrinsic lability of different sulfonate esters, identifying new sulfonate protecting groups and mild, selective cleavage conditions...
  3. pmc Synthesis of near-IR fluorescent oxazine dyes with esterase-labile sulfonate esters
    Steven M Pauff
    Department of Biochemistry and Molecular Pharmacology, University of Massachusetts Medical School, Worcester, Massachusetts 01655, USA
    Org Lett 13:6196-9. 2011
    ....
  4. pmc A trifluoroacetic acid-labile sulfonate protecting group and its use in the synthesis of a near-IR fluorophore
    Steven M Pauff
    Department of Biochemistry and Molecular Pharmacology, University of Massachusetts Medical School, 364 Plantation Street, Worcester, Massachusetts 01605, USA
    J Org Chem 78:711-6. 2013
    ..The use of this protecting group improved the synthesis of a sulfonated near-IR fluorophore and the mild deprotection conditions allowed isolation of the product without requiring chromatography...
  5. doi request reprint Design and application of esterase-labile sulfonate protecting groups
    Laert Rusha
    Department of Biochemistry and Molecular Pharmacology, University of Massachusetts Medical School, 364 Plantation St, Worcester, MA 01605, USA
    Chem Commun (Camb) 47:2038-40. 2011
    ..Three esterase-labile, but chemically-stable sulfonate protecting groups have been designed and synthesized. One of these sulfonate esters allowed the cytoplasmic delivery and unmasking of a sulfonated dye in live cells...