John Sherman

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John Sherman

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Research and Teaching Interests

Professor Sherman is interested in the design and synthesis of organic and biological molecules that have well-defined structure. These compounds are designed to explore molecular recognition and to probe the factors governing protein folding.

One project involves the creation of a new system of hybrid cavitand-proteins or 'caviteins' (pictured). These de novo proteins are composed of four alpha-helical peptide chains that are organized into a bundle by a rigid bowl-shaped organic macrocyclic cavitand molecule. This cavitand moiety creates an enforced cavity suitable for complexation of guest molecules while the helices form a super-secondary protein structure atop the hydrophobic cavity. The caviteins are designed to selectively bind guest molecules such as amino acids, to catalyze reactions such as amide hydrolysis, and to help elucidate some of the interactions that are important in promoting super-secondary structure in proteins.

A second research area explores the reaction mechanism and templation effects responsible for the formation of carceplexes. Carceplexes are closed-surface organic molecules that permenantly entrap smaller molecules within their confines. The wate r solubilization of carceplexes will unleash entirely new areas of study including applications such as drug delivery.

Another project entails the creation of a new family of self-assembling structures (SAS's). SAS's are ubiquitous in nature (e.g., DNA double helix, cell membranes, etc.) and are receiving great attention in materials science (e.g., monolayers, liquid crystals, etc.). We are covalently linking bowl-shaped molecules and studying their aggregation to form 1-D rods and 2-D bilayers.

Techniques employed in this lab include organic synthesis, peptide synthesis, operation of and analysis by HPLC, NMR and circular dichroism.

Contact

Real name: 
Email: 
Office Room Number(s): 
E216
Office Phone Number: 
604-822-2305
Fax Number: 
604-822-2847

Curriculum Vitae

B.A., Haverford College (1983); Ph.D., University of California, Los Angeles (D.J. Cram, 1988); Research Associate, The Rockefeller University (E.T. Kaiser, 1988-89); NIH Postdoctoral Fellow, New York University (N.R. Kallenbach, 1989-91).

Publications

2009

Freeman, J. O. ; Lee, W. C. ; Murphy, M. E. P. ; Sherman, J. C. X-Ray Crystal Analysis Of A Tasp: Structural Insights Of A Cavitein Dimer. Journal of the American Chemical Society 2009, 131, 7421-7429.
Nikan, M. ; Sherman, J. C. Cation-Complexation Behavior Of Template-Assembled Synthetic G-Quartets. Journal of Organic Chemistry 2009, 74, 5211-5218.
Sun, J. Y. ; Patrick, B. O. ; Sherman, J. C. A New [4]Carceplex, And A Crystal Structure And Dynamic Combinatorial Chemistry Of A [5]Carceplex. Tetrahedron 2009, 65, 7296-7302.

2008

Nikan, M. ; Sherman, J. C. Template-Assembled Synthetic G-Quartets (Tasqs). Angewandte Chemie-International Edition 2008, 47, 4900-4902.

2007

Huttunen-Hennelly, H. E. K. ; Sherman, J. C. The Design, Synthesis, And Characterization Of The First Cavitand-Based De Novo Hetero-Template-Assembled Synthetic Proteins (Hetero-Tasps). Organic & Biomolecular Chemistry 2007, 5, 3637-3650.
Sherman, J. C. Donald J. Cram. Chemical Society Reviews 2007, 36, 148-150.
Freeman, J. O. ; Wallhorn, D. ; Sherman, J. C. Four-Helix Bundle Cavitein Reveals Middle Leucine As Linchpin. Biopolymers 2007, 88, 725-732.
Seo, E. S. ; Scott, W. R. P. ; Straus, S. K. ; Sherman, J. C. Optimal Attachment Position And Linker Length Promote Native-Like Character Of Cavitand-Based Template-Assembled Synthetic Proteins (Tasps). Chemistry-a European Journal 2007, 13, 3596-3605.

2006

Scott, W. R. P. ; Seo, E. ; Huttunen, H. ; Wallhorn, D. ; Sherman, J. C. ; Straus, S. K. Characterization Of De Novo Four-Helix Bundles By Molecular Dynamics Simulations. Proteins-Structure Function and Bioinformatics 2006, 64, 719-729.

2005

Makeiff, D. A. ; Sherman, J. C. A Six-Bowl Carceplex That Entraps Seven Guest Molecules. Journal of the American Chemical Society 2005, 127, 12363-12367.

2004

Scott, W. R. ; Seo, E. ; Huttunen, H. ; Wallhorn, D. ; Sherman, J. C. ; Straus, S. K. Characterization Of De Novo Four-Helix Bundles By Molecular Dynamics Simulations. Protein Science 2004, 13, 343.
Seo, E. S. ; Sherman, J. C. Cavitand Based Four-Helix Bundles. In Peptide Revolution: Genomics, Proteomics & Therapeutics; Chorev, M. ; Sawyer, T. K. ; Peptide Revolution: Genomics, Proteomics & Therapeutics; Amer Chemical Soc: Washington, 2004; pp. 246-247.
Huttunen, H. K. ; Sherman, J. C. De Novo Four-Helix Bundle Proteins. In Peptide Revolution: Genomics, Proteomics & Therapeutics; Chorev, M. ; Sawyer, T. K. ; Peptide Revolution: Genomics, Proteomics & Therapeutics; Amer Chemical Soc: Washington, 2004; pp. 244-245.

2003

Makeiff, D. A. ; Sherman, J. C. Template Effect Where 1-3 Molecules Drive Formation Of A Trimer Carceplex. Chemistry-a European Journal 2003, 9, 3253-3262.
Makeiff, D. A. ; Vishnumurthy, K. ; Sherman, J. C. Ketonization Of Incarcerated Acetophenone Enol. Journal of the American Chemical Society 2003, 125, 9558-9559.
Seo, E. S. ; Sherman, J. C. Cavitand Based Four-Helix Bundles. Biopolymers 2003, 71, P062.
Huttunen, H. K. ; Sherman, J. C. De Novo Four-Helix Bundle Proteins. Biopolymers 2003, 71, P067.
Sherman, J. Molecules That Can’T Resist Templation. Chemical Communications 2003, 1617-1623.

2002

Causton, A. S. ; Sherman, J. C. A Comparison Of Three- And Four-Helix Bundle Tasp Molecules. Journal of Peptide Science 2002, 8, 275-282.
Naumann, C. ; Place, S. ; Sherman, J. C. Synthesis And Characterization Of A Disulfide-Linked C-5-Symmetric [5]Carceplex. Journal of the American Chemical Society 2002, 124, 16-17.
Naumann, C. ; Patrick, B. O. ; Sherman, J. C. Synthesis And Conformational Dynamics Of Ortho-Xylyl-Bridged-[4]Cavitands. Tetrahedron 2002, 58, 787-798.
Naumann, C. ; Patrick, B. O. ; Sherman, J. Synthesis And Characterization Of Upper And Lower Rim Functionalized [6]Cavitands. Chemistry-a European Journal 2002, 8, 3717-3723.
Mungaroo, R. ; Sherman, J. C. Formation Of A Tris-Capsule And A Tris-Carceplex From A Cyclic Six-Bowl Assembly. Chemical Communications 2002, 1672-1673.

2001

Gui, X. ; Sherman, J. C. Host-Guest Binding Of Simple Cavitands In Water. Chemical Communications 2001, 2680-2681.
Naumann, C. ; Roman, E. ; Peinador, C. ; Ren, T. ; Patrick, B. O. ; Kaifer, A. E. ; Sherman, J. C. Expanding Cavitand Chemistry: The Preparation And Characterization Of [N]Cavitands With N >= 4. Chemistry-a European Journal 2001, 7, 1637-1645.

2000

Wallhorn, D. ; Mezo, A. R. ; Sherman, J. C. Cavitand Templated De Novo Four-Helix Bundles. In Peptides for the New Millennium; Fields, G. B. ; Tam, J. P. ; Barany, G. ; Peptides for the New Millennium; Springer: Dordrecht, 2000; pp. 295-296.
Chapman, R. G. ; Sherman, J. C. Restricted Motion Of Guests Confined In Carceplexes And Capsules. Journal of Organic Chemistry 2000, 65, 513-516.
Makeiff, D. A. ; Pope, D. J. ; Sherman, J. C. Template Effects In The Formation Of A Tetramethylene-Bridged Hemicarceplex. Journal of the American Chemical Society 2000, 122, 1337-1342.
Chopra, N. ; Naumann, C. ; Sherman, J. C. Bis-Capsules: Cooperative Reversible Encapsulation Of Two Molecules In Adjacent Separate Chambers. Angewandte Chemie-International Edition 2000, 39, 194-+.

1999

Mezo, A. R. ; Sherman, J. C. Cavitands Are Effective Templates For Inducing Stability And Nativelike Structure In De Novo Four-Helix Bundles. Journal of the American Chemical Society 1999, 121, 8983-8994.
Chapman, R. G. ; Sherman, J. C. Elucidation Of "twistomers" In Container Compounds. Journal of the American Chemical Society 1999, 121, 1962-1963.
Causton, A. S. ; Sherman, J. C. Design Of Proteins Using Rigid Organic Macrocycles As Scaffolds. Bioorganic & Medicinal Chemistry 1999, 7, 23-27.
Jasat, A. ; Sherman, J. C. Carceplexes And Hemicarceplexes. Chemical Reviews 1999, 99, 931-967.
Chopra, N. ; Sherman, J. C. A Giant Carceplex Permanently Entraps Three Organic Molecules. Angewandte Chemie-International Edition 1999, 38, 1955-1957.

1998

Chapman, R. G. ; Sherman, J. C. Reversible Molecular Capsules Composed Of Two Cavitands Linked Via An Assortment Of Charged-Hydrogen Bonds And Covalent Bonds. Journal of the American Chemical Society 1998, 120, 9818-9826.
Chapman, R. G. ; Sherman, J. C. Templation In The Formation Of Carceplexes. Journal of Organic Chemistry 1998, 63, 4103-4110.
Chapman, R. G. ; Olovsson, G. ; Trotter, J. ; Sherman, J. C. Crystal Structure And Thermodynamics Of Reversible Molecular Capsules. Journal of the American Chemical Society 1998, 120, 6252-6260.

1997

Chopra, N. ; Sherman, J. C. A Bis(Carceplex) From A Cyclic Tetramer Of Cavitands. Angewandte Chemie-International Edition in English 1997, 36, 1727-1729.
Sherman, J. C. Self-Assembly Of Two Or More Cavitands. Gazzetta Chimica Italiana 1997, 127, 653-655.
Chapman, R. G. ; Sherman, J. C. Templation And Encapsulation In Supramolecular Chemistry. Tetrahedron 1997, 53, 15911-15945.
Nakamura, K. ; Sheu, C. M. ; Keating, A. E. ; Houk, K. N. ; Sherman, J. C. ; Chapman, R. G. ; Jorgensen, W. L. Self-Assembling Ternary Complex Stabilities And Template Ratios In Carceplex Formation. Journal of the American Chemical Society 1997, 119, 4321-4322.

1996

Gibb, B. C. ; Chapman, R. G. ; Sherman, J. C. Synthesis Of Hydroxyl-Footed Cavitands. Journal of Organic Chemistry 1996, 61, 1505-1509.

1995

Gibb, B. C. ; Mezo, A. R. ; Sherman, J. C. Prototype For A New Family Of De-Novo Proteins. Tetrahedron Letters 1995, 36, 7587-7590.
Fraser, J. R. ; Borecka, B. ; Trotter, J. ; Sherman, J. C. An Asymmetric Carceplex And New Crystal-Structure Yield Information Regarding A 1-Million-Fold Template Effect. Journal of Organic Chemistry 1995, 60, 1207-1213.
Gibb, B. C. ; Mezo, A. R. ; Causton, A. S. ; Fraser, J. R. ; Tsai, F. C. S. ; Sherman, J. C. Efficient Coupling Of Amino-Acid Derivatives To Rigid Organic Scaffolds - Model Syntheses For De-Novo Proteins. Tetrahedron 1995, 51, 8719-8732.
Chopra, N. ; Sherman, J. C. Templation Effects On Formation Of A Hemicarceplex. Supramolecular Chemistry 1995, 5, 31-37.
Sherman, J. C. Two Shells About A Nut: Carceplexes, Hemicarceplexes And Highly Stable Ternary Complexes. In Supramolecular Stereochemistry; Siegel, J. S. ; Supramolecular Stereochemistry; Kluwer Academic Publ: Dordrecht, 1995; Vol. 473, pp. 233-238.
Chapman, R. G. ; Sherman, J. C. Study Of Templation And Molecular Encapsulation Using Highly Stable And Guest-Selective Self-Assembling Structures. Journal of the American Chemical Society 1995, 117, 9081-9082.

1994

Chapman, R. G. ; Chopra, N. ; Cochien, E. D. ; Sherman, J. C. Carceplex Formation - Scope Of A Remarkably Efficient Encapsulation Reaction. Journal of the American Chemical Society 1994, 116, 369-370.

1993

Tsai, F. C. S. ; Sherman, J. C. Circular-Dichroism Analysis Of A Synthetic Peptide Corresponding To The Alpha,alpha-Corner Motif Of Hemoglobin. Biochemical and Biophysical Research Communications 1993, 196, 435-439.