Scott Miller

Summary

Affiliation: Yale University
Country: USA

Publications

  1. ncbi request reprint Studies of folded peptide-based catalysts for asymmetric organic synthesis
    Jarred T Blank
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 3860, USA
    Biopolymers 84:38-47. 2006
  2. pmc Combinatorial evolution of site- and enantioselective catalysts for polyene epoxidation
    Phillip A Lichtor
    Department of Chemistry, Yale University, PO Box 208107, New Haven, Connecticut 06520 8107, USA
    Nat Chem 4:990-5. 2012
  3. pmc An efficient chemical synthesis of carboxylate-isostere analogs of daptomycin
    Sabesan Yoganathan
    Department of Chemistry, Yale University, P O Box 208107, New Haven, Connecticut 06520, USA
    Org Biomol Chem 11:4680-5. 2013
  4. ncbi request reprint Asymmetric catalysis mediated by synthetic peptides
    Elizabeth A Colby Davie
    Department of Chemistry, Yale University, P O Box 208107, New Haven, Connecticut 06520 8107, USA
    Chem Rev 107:5759-812. 2007
  5. pmc A case of remote asymmetric induction in the peptide-catalyzed desymmetrization of a bis(phenol)
    Chad A Lewis
    Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA
    J Am Chem Soc 130:16358-65. 2008
  6. ncbi request reprint Structure-selectivity relationships and structure for a peptide-based enantioselective acylation catalyst
    Matthew B Fierman
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467 3860, USA
    J Am Chem Soc 126:6967-71. 2004
  7. pmc Disparate behavior of carbonyl and thiocarbonyl compounds: acyl chlorides vs thiocarbonyl chlorides and isocyanates vs isothiocyanates
    Kenneth B Wiberg
    Department of Chemistry, Yale University, New Haven, Connecticut 06520 8107, USA
    J Org Chem 74:3659-64. 2009
  8. ncbi request reprint Desymmetrization of glycerol derivatives with peptide-based acylation catalysts
    Chad A Lewis
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA
    Org Lett 7:3021-3. 2005
  9. pmc Dynamic kinetic resolution of biaryl atropisomers via peptide-catalyzed asymmetric bromination
    Jeffrey L Gustafson
    Department of Chemistry, Yale University, 225 Prospect Street, Post Office Box 208107, New Haven, CT 06520 8107, USA
    Science 328:1251-5. 2010
  10. ncbi request reprint Enantioselective synthesis of an aziridinomitosane and selective functionalizations of a key intermediate
    Nikolaos Papaioannou
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467 3860, USA
    J Org Chem 68:2728-34. 2003

Research Grants

Collaborators

  • RONALD RAINES
  • Karl B Hansen
  • Yingju Xu
  • P A Wender
  • William F Bailey
  • Kenneth B Wiberg
  • MATTHEW SIGMAN
  • Wayne E Steinmetz
  • Gorka Peris
  • Chad A Lewis
  • Bryan J Cowen
  • Jeffrey L Gustafson
  • Adam J Morgan
  • Steven M Mennen
  • Charles E Jakobsche
  • Carrie E Aroyan
  • Bianca R Sculimbrene
  • Melissa M Vasbinder
  • Sabesan Yoganathan
  • Jarred T Blank
  • Phillip A Lichtor
  • Brandon S Fowler
  • Christina M Longo
  • Benjamin C Gorske
  • María Sánchez-Roselló
  • Jaume Balsells
  • David Pollard
  • Jerry Murry
  • Elizabeth A Colby Davie
  • Robert A Reamer
  • Anna Chiu
  • Mary F Roberts
  • Cara L Jenkins
  • Matthew B Fierman
  • Nikolaos Papaioannou
  • Jason E Imbriglio
  • Catherine A Evans
  • David J Guerin
  • Michael F Mesleh
  • Yu Gui Gu
  • Yong He
  • Ning Yin
  • Daniel Lim
  • Alpay Dermenci
  • Amit Choudhary
  • Peter J Mikochik
  • Yang Wei
  • Curren T Mbofana
  • Kate E Longcore
  • Lindsey B Saunders
  • Angela L A Puchlopek
  • Janie Merkel
  • Michele Kubryk
  • Craig K Esser
  • Shio Komiya
  • Yoona R Kim
  • John D Gipson
  • Yangling Karen Wang
  • Daniel J O'Leary

Detail Information

Publications41

  1. ncbi request reprint Studies of folded peptide-based catalysts for asymmetric organic synthesis
    Jarred T Blank
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 3860, USA
    Biopolymers 84:38-47. 2006
    ..Of note, turns, helices, nonobvious folds, and still undetermined secondary structures characterize the structural and functionally diverse motifs that enable peptide-catalyzed asymmetric reactions to occur...
  2. pmc Combinatorial evolution of site- and enantioselective catalysts for polyene epoxidation
    Phillip A Lichtor
    Department of Chemistry, Yale University, PO Box 208107, New Haven, Connecticut 06520 8107, USA
    Nat Chem 4:990-5. 2012
    ..Moreover, the approach culminated in catalysts that exhibit alternative-site selectivity in comparison to oxidation catalysts previously described...
  3. pmc An efficient chemical synthesis of carboxylate-isostere analogs of daptomycin
    Sabesan Yoganathan
    Department of Chemistry, Yale University, P O Box 208107, New Haven, Connecticut 06520, USA
    Org Biomol Chem 11:4680-5. 2013
    ..The present study also describes an esterification protocol to overcome the possible backbone cyclization of the activated side chain carboxylic acid group of either Asp or Glu onto the backbone amide. ..
  4. ncbi request reprint Asymmetric catalysis mediated by synthetic peptides
    Elizabeth A Colby Davie
    Department of Chemistry, Yale University, P O Box 208107, New Haven, Connecticut 06520 8107, USA
    Chem Rev 107:5759-812. 2007
  5. pmc A case of remote asymmetric induction in the peptide-catalyzed desymmetrization of a bis(phenol)
    Chad A Lewis
    Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA
    J Am Chem Soc 130:16358-65. 2008
    ....
  6. ncbi request reprint Structure-selectivity relationships and structure for a peptide-based enantioselective acylation catalyst
    Matthew B Fierman
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467 3860, USA
    J Am Chem Soc 126:6967-71. 2004
    ..In addition, an experimentally derived solution structure of the peptide-based catalyst is presented that supports a key role for each residue within the peptide chain...
  7. pmc Disparate behavior of carbonyl and thiocarbonyl compounds: acyl chlorides vs thiocarbonyl chlorides and isocyanates vs isothiocyanates
    Kenneth B Wiberg
    Department of Chemistry, Yale University, New Haven, Connecticut 06520 8107, USA
    J Org Chem 74:3659-64. 2009
    ..Information concerning differences in reactivity was derived from analysis of Hirshfeld atomic charge distributions and calculated hydrogenolysis reaction energies...
  8. ncbi request reprint Desymmetrization of glycerol derivatives with peptide-based acylation catalysts
    Chad A Lewis
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA
    Org Lett 7:3021-3. 2005
    ..Enantiomeric excesses of up to 97% have been obtained for the monoacylated products. A range of other substrates have been examined that shed light on the mechanistic basis of the desymmetrizations...
  9. pmc Dynamic kinetic resolution of biaryl atropisomers via peptide-catalyzed asymmetric bromination
    Jeffrey L Gustafson
    Department of Chemistry, Yale University, 225 Prospect Street, Post Office Box 208107, New Haven, CT 06520 8107, USA
    Science 328:1251-5. 2010
    ..A mechanistic model is advanced that accounts for the basis of selectivity observed...
  10. ncbi request reprint Enantioselective synthesis of an aziridinomitosane and selective functionalizations of a key intermediate
    Nikolaos Papaioannou
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467 3860, USA
    J Org Chem 68:2728-34. 2003
    ..Optically pure material was then converted to the mitosane core, which was the subject of additional studies on the selective modification to produce several substituted compounds containing a mitosane ring system...
  11. ncbi request reprint Site-selective derivatization and remodeling of erythromycin A by using simple peptide-based chiral catalysts
    Chad A Lewis
    Department of Chemistry, Boston College, Chestnut Hill, MA 02467, USA
    Angew Chem Int Ed Engl 45:5616-9. 2006
  12. doi request reprint Pyridylalanine (pal)-peptide catalyzed enantioselective allenoate additions to N-acyl imines
    Bryan J Cowen
    Department of Chemistry, Yale University, P O Box 208107, New Haven, Connecticut 06520 8107, USA
    J Am Chem Soc 131:6105-7. 2009
    ..The unique allenic products are obtained with enantiomer ratios of up to approximately 95:5 (up to >98:2 following recrystallization)...
  13. ncbi request reprint Remote desymmetrization at near-nanometer group separation catalyzed by a miniaturized enzyme mimic
    Chad A Lewis
    Department of Chemistry, Yale University, New Haven, CT 06520, USA
    J Am Chem Soc 128:16454-5. 2006
    ..We report here a synthetic, miniaturized enzyme mimic that catalyzes a desymmetrization reaction over a very long distance...
  14. pmc Regio- and stereoselective synthesis of fluoroalkenes by directed Au(I) catalysis
    Benjamin C Gorske
    Department of Chemistry, Yale University, P O Box 208107, New Haven, Connecticut 06520, USA
    Org Lett 11:4318-21. 2009
    ..Additional experiments with two directing groups installed have established some initial principles with respect to a hierarchy of directing groups and their capacity for influencing hydrofluorination regioselectivity...
  15. pmc Catalytic site-selective synthesis and evaluation of a series of erythromycin analogs
    Chad A Lewis
    Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520 8107, USA
    Bioorg Med Chem Lett 18:6007-11. 2008
    ..The semi-synthetic analogs were subjected to MIC evaluation with two bacterial strains and compared to unfunctionalized EryA...
  16. pmc An approach to the site-selective diversification of apoptolidin A with peptide-based catalysts
    Chad A Lewis
    Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520 8107, USA
    J Nat Prod 72:1864-9. 2009
    ..Biological evaluation of the new apoptolidin analogues was then conducted using growth inhibition assays based on the H292 human lung carcinoma cell line. The new analogues exhibited activities comparable to apoptolidin A...
  17. doi request reprint Development of a cysteine-catalyzed enantioselective Rauhut-Currier reaction
    Carrie E Aroyan
    Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA
    J Org Chem 75:5784-96. 2010
    ..Also included is a brief survey of the reaction scope involving different ring sizes as well as functionalized substrates...
  18. ncbi request reprint Enantiodivergence in small-molecule catalysis of asymmetric phosphorylation: concise total syntheses of the enantiomeric D-myo-inositol-1-phosphate and D-myo-inositol-3-phosphate
    Bianca R Sculimbrene
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 3860, USA
    J Am Chem Soc 124:11653-6. 2002
    ..The systematic discovery of site-selective catalysts establishes a basis for future studies of chiral catalysts that differentiate unique functional groups in polyfunctional molecules...
  19. pmc Aspartate-catalyzed asymmetric epoxidation reactions
    Gorka Peris
    Department of Chemistry, Yale University, P O Box 208107, New Haven, Connecticut 06520 8107, USA
    J Am Chem Soc 129:8710-1. 2007
  20. pmc Linear free-energy relationship analysis of a catalytic desymmetrization reaction of a diarylmethane-bis(phenol)
    Jeffrey L Gustafson
    Department of Chemistry, Yale University, P O Box 208107, New Haven, Connecticut 06520 8107, USA
    Org Lett 12:2794-7. 2010
    ..The potential origin of this observation and the role of different steric parameters are discussed...
  21. pmc Peptide-catalyzed kinetic resolution of formamides and thioformamides as an entry to nonracemic amines
    Brandon S Fowler
    Department of Chemistry, Yale University, P O Box 208107, New Haven, Connecticut 06520 8107, USA
    J Am Chem Soc 132:2870-1. 2010
    ..The products of these asymmetric reactions were shown to be readily converted to desirable building blocks such as N-Boc-amines and the parent chiral formamide compounds...
  22. ncbi request reprint Peptide bond isosteres: ester or (E)-alkene in the backbone of the collagen triple helix
    Cara L Jenkins
    Department of Chemistry, University of Wisconsin Madison, Madison, Wisconsin 53706, USA
    Org Lett 7:2619-22. 2005
    ..Thus, this recurring hydrogen bond is critical to the structural integrity of collagen. In this context, an ester isostere confers more stability than does an (E)-alkene...
  23. ncbi request reprint Dual catalyst control in the amino acid-peptide-catalyzed enantioselective Baylis-Hillman reaction
    Jason E Imbriglio
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA
    Org Lett 5:3741-3. 2003
    ..Although neither compound is effective independently in terms of rate or enantioselectivity, their combination leads to catalysis where enantioselectivities up to 81% have been observed...
  24. ncbi request reprint Enantioselective catalysis and complexity generation from allenoates
    Bryan J Cowen
    Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520 8107, USA
    Chem Soc Rev 38:3102-16. 2009
    ..This tutorial review will describe these methodologies, with a special emphasis on recent work regarding asymmetric reactions using chiral Lewis base catalysts...
  25. pmc Functional analysis of an aspartate-based epoxidation catalyst with amide-to-alkene peptidomimetic catalyst analogues
    Charles E Jakobsche
    Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520 4900, USA
    Angew Chem Int Ed Engl 47:6707-11. 2008
  26. ncbi request reprint Thiazolylalanine-derived catalysts for enantioselective intermolecular aldehyde-imine cross-couplings
    Steven M Mennen
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 3860, USA
    J Am Chem Soc 127:1654-5. 2005
    ..The use of a hindered base to suppress product racemization was stimulated by a mechanistic study that revealed an isotope effect on the racemization rate of the product...
  27. ncbi request reprint Unified total syntheses of the inositol polyphosphates: D-I-3,5,6P3, D-I-3,4,5P3, D-I-3,4,6P3, and D-I-3,4,5,6P4 via catalytic enantioselective and site-selective phosphorylation
    Adam J Morgan
    Department of Chemistry, Boston College, Chestnut Hill, MA 02467, USA
    J Org Chem 71:6923-31. 2006
    ..The syntheses described herein exploit a common intermediate to gain efficient access to eight unique inositol polyphosphates...
  28. ncbi request reprint Enantioselective Rauhut-Currier reactions promoted by protected cysteine
    Carrie E Aroyan
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467 3860, USA
    J Am Chem Soc 129:256-7. 2007
  29. ncbi request reprint Synthesis of the pro-gly dipeptide alkene isostere using olefin cross-metathesis
    Melissa M Vasbinder
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467 3860, USA
    J Org Chem 67:6240-2. 2002
    ..Treatment of the two partners in an optimized molar ratio affords the cross product 1 (83% yield). Three other examples are demonstrated to evaluate the potential of the approach...
  30. ncbi request reprint Asymmetric azidation-cycloaddition with open-chain peptide-based catalysts. A sequential enantioselective route to triazoles
    David J Guerin
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467 3860, USA
    J Am Chem Soc 124:2134-6. 2002
    ....
  31. ncbi request reprint Enantioselective [3+2]-cycloadditions catalyzed by a protected, multifunctional phosphine-containing alpha-amino acid
    Bryan J Cowen
    Department of Chemistry, Yale University, P O Box 208107, New Haven, Connecticut 06520 8107, USA
    J Am Chem Soc 129:10988-9. 2007
  32. ncbi request reprint Chemistry and biology of deoxy-myo-inositol phosphates: stereospecificity of substrate interactions within an archaeal and a bacterial IMPase
    Adam J Morgan
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467 3860, USA
    J Am Chem Soc 126:15370-1. 2004
    ..These new probes also allow a prediction of the active site binding mode of the substrate for the Escherichia coli IMPase for which no crystal structure exists...
  33. ncbi request reprint Proton-activated fluorescence as a tool for simultaneous screening of combinatorial chemical reactions
    Catherine A Evans
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467 3860, USA
    Curr Opin Chem Biol 6:333-8. 2002
    ..Given the range of reactions that may be set up to provide a change in local pH, the potential of PAF to facilitate catalyst discovery and process development is significant...
  34. ncbi request reprint Asymmetric syntheses of phosphatidylinositol-3-phosphates with saturated and unsaturated side chains through catalytic asymmetric phosphorylation
    Bianca R Sculimbrene
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467 3860, USA
    J Am Chem Soc 126:13182-3. 2004
    ..Syntheses in each enantiomeric series are reported that rely on the choice of enantioselective peptide-based catalyst to define the enantiomeric series in which the syntheses are carried out...
  35. pmc n --> pi* Interaction and n)(pi Pauli repulsion are antagonistic for protein stability
    Charles E Jakobsche
    Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA
    J Am Chem Soc 132:6651-3. 2010
    ....
  36. ncbi request reprint A nonenzymatic acid/peracid catalytic cycle for the Baeyer-Villiger oxidation
    Gorka Peris
    Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA
    Org Lett 10:3049-52. 2008
    ..A singular example of a chiral catalyst demonstrates, in principle, that enantioselective catalysis will be possible with this strategy for catalyst turnover...
  37. ncbi request reprint Streamlined synthesis of phosphatidylinositol (PI), PI3P, PI3,5P2, and deoxygenated analogues as potential biological probes
    Yingju Xu
    Department of Chemistry, Boston College, Chestnut Hill, Massachusetts 02467, USA
    J Org Chem 71:4919-28. 2006
    ..These syntheses set the stage for high-precision biological investigations of polar headgroup/biological target interactions of these membrane-associated signaling molecules...
  38. ncbi request reprint Development of a bio-inspired acyl-anion equivalent macrocyclization and synthesis of a trans-resorcylide precursor
    Steven M Mennen
    Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467 3860, USA
    J Org Chem 72:5260-9. 2007
    ..These findings were applied to a range of substrates, including the synthesis of a key intermediate in a rapid synthesis of trans-resorcylide...
  39. doi request reprint Site-selective catalysis of phenyl thionoformate transfer as a tool for regioselective deoxygenation of polyols
    María Sánchez-Roselló
    Department of Chemistry, Yale University, PO Box 208107, New Haven, Connecticut 06520 8107, USA
    J Org Chem 73:1774-82. 2008
    ..Through screening of peptides and control of reaction conditions, products could be observed that reflected both the inherent preference of substrates and also reversal of inherent selectivity...
  40. pmc Asymmetric Syntheses of L,L- and L,D-di-myo-inositol-1,1'-phosphate and their behavior as stabilizers of enzyme activity at extreme temperatures
    Christina M Longo
    Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520 4900, USA
    Angew Chem Int Ed Engl 48:4158-61. 2009
    ..The differential ability of each isomer to contribute to thermoprotection in the context of a key enzyme has been assessed and both isomers of DIP are shown to possess biological activity...
  41. ncbi request reprint DNA as a template for reaction discovery
    Scott J Miller
    Nat Biotechnol 22:1378-9. 2004

Research Grants15

  1. Site-Selective Catalysts for Organic Synthesis
    Scott J Miller; Fiscal Year: 2010
    ....
  2. Site-Selective Catalysts for Organic Synthesis
    Scott Miller; Fiscal Year: 2009
    ....
  3. Site-Selective Catalysts for Organic Synthesis
    Scott Miller; Fiscal Year: 2007
    ....
  4. Site-Selective Catalysts for Organic Synthesis
    Scott Miller; Fiscal Year: 2005
    ..The end result will be both new tools for the selective synthesis of complex biologically active compounds, as well as important samples for use in biological screens. ..
  5. Selective Peptide-Based Oxidation Catalysts for Bioactive Molecule Synthesis
    Scott J Miller; Fiscal Year: 2011
    ..Success in this endeavor will enable efficient synthesis of complex, biologically active molecules. A particular emphasis will be on natural product diversification, which is a long-standing problem in the field of medicinal chemistry. ..
  6. Site-Selective Catalysts for Organic Synthesis
    Scott Miller; Fiscal Year: 2004
    ..The end result will be both new tools for the selective synthesis of complex biologically active compounds, as well as important samples for use in biological screens. ..
  7. ASYMMETRIC ENOLSILANE COUPLING REACTIONS
    Scott Miller; Fiscal Year: 2002
    ..Our objective is to develop reactions that will introduce as many of the stereogenic centers in these systems as possible with single chemical reactions. ..
  8. ASYMMETRIC ENOLSILANE COUPLING REACTIONS
    Scott Miller; Fiscal Year: 2000
    ..Our objective is to develop reactions that will introduce as many of the stereogenic centers in these systems as possible with single chemical reactions. ..
  9. ASYMMETRIC ENOLSILANE COUPLING REACTIONS
    Scott Miller; Fiscal Year: 1999
    ..Our objective is to develop reactions that will introduce as many of the stereogenic centers in these systems as possible with single chemical reactions. ..
  10. Site-Selective Catalysts for Organic Synthesis
    Scott Miller; Fiscal Year: 2006
    ..The end result will be both new tools for the selective synthesis of complex biologically active compounds, as well as important samples for use in biological screens. ..
  11. Site-Selective Catalysts for Organic Synthesis
    Scott Miller; Fiscal Year: 2003
    ..The end result will be both new tools for the selective synthesis of complex biologically active compounds, as well as important samples for use in biological screens. ..
  12. ASYMMETRIC ENOLSILANE COUPLING REACTIONS
    Scott Miller; Fiscal Year: 2001
    ..Our objective is to develop reactions that will introduce as many of the stereogenic centers in these systems as possible with single chemical reactions. ..
  13. Site-Selective Catalysts for Organic Synthesis
    Scott Miller; Fiscal Year: 2005
    ..The end result will be both new tools for the selective synthesis of complex biologically active compounds, as well as important samples for use in biological screens. ..