bio-organic chemistry amino acids medicinal chemistry heterocycles peptide mimicry

The Lubell laboratory performs research in medicinal chemistry and peptide science, with particular interest in the development of novel effective methods for the synthesis of heterocycles, amino acids, peptides and peptide mimics.

Luo, J.; Pardin, C.; Lubell, W. D.; Zhu, X. X. “Poly(vinyl alcohol)-graft-poly(ethylene glycol) resins and their use in solid-phase synthesis and supported TEMPO catalysis”, Chem. Commun., 2007, 21, 2136-2138.Lien - Article - Link

Dorr, A.; Lubell, W. D. “Synthesis of a new p-deficient phenylalanine derivative from a common 1,4-diketone intermediate and study of the influence of aromatic density on prolyl amide isomer population”, Biopolymers, 2007, 88(2), 290-299. Lien - Article - Link

Boeglin, D.; Hamdan, F. F.; Melendez, R. E.; Cluzeau, J.; Laperriere, A.; Heroux, M.; Bouvier, M.; Lubell, W. D. “Calcitonin gene-related peptide analogues with aza and indolizidinone amino acid residues reveal conformational requirements for antagonist activity at the human calcitonin gene-related peptide 1 receptor”, J. Med. Chem., 2007, 50(6), 1401-1408. Lien - Article - Link

Rao, Mallem H. V. R.; Pinyol, E.; Lubell, W. D. “Rigid dipeptide mimics: synthesis of enantiopure C6-functionalized pyrrolizidinone amino acids”, J. Org. Chem., 2007, 72(3), 736-743. Lien - Article - Link

Jolicoeur, B.; Lubell, W. D. “4-Alkoxy- and 4-amino-2,2'-bipyrrole synthesis”, Org. Lett., 2006, 8(26), 6107-6110. Lien - Article - Link

Jolicoeur, B.; Chapman, E. E.; Thompson, A.; Lubell, W. D. “Pyrrole protection”, Tetrahedron, 2006, 62(50), 11531-11563. Lien - Article - Link

Iden, H. S.; Lubell, W. D. “1,4-Diazepinone and Pyrrolodiazepinone Syntheses via Homoallylic Ketones from Cascade Addition of Vinyl Grignard Reagent to a-Aminoacyl-b-amino Esters”, Org. Lett., 2006, 8(16), 3425-3428. Lien - Article - Link

Surprenant, S.; Lubell, William D. “From Macrocycle Dipeptide Lactams To Azabicyclo[X.Y.0]alkanone Amino Acids: A Transannular Cyclization Route for Peptide Mimic Synthesis”, Org. Lett., 2006, 8(13), 2851-2854. Lien - Article - Link

Surprenant, S.; Lubell, W. D. "9-(4-Bromophenyl)-9-fluorenyl as a Safety-Catch Nitrogen Protecting Group" J. Org. Chem. 2006, 71(2), 848-851.Lien - Article - Link

Brouillette, Y.; Rombouts, F. J. R.; Lubell, W. D. "Solid-Phase Synthesis of 3-Aminopyrrole-2,5-dicarboxylate Analogs" J. Comb. Chem. 2006, 8(1), 117-126. Lien - Article - Link

Lubell, W.D., Blankenship, J.W., Fridkin, G., Kaul, R. (2005) Peptides. Science of Synthesis 21.11, Chemistry of Amides. Thieme, Stuttgart, 713-809.

Hansford, K. A.; Guarin, S. A. P., Skene, W. G.; Lubell, W. D. "Bis(pyrrol-2-yl)arylenes from the Tandem Bi-directional Addition of Vinyl Grignard Reagents to Aryldiesters" J. Org. Chem. 2005, 70, 7996-8000. Lien - Article - Link

Boeglin, D.; Lubell, W. D. "Aza-Amino Acid Scanning of Secondary Structure Suited for Solid-Phase Peptide Synthesis with Fmoc Chemistry and Aza-Amino Acids with Heteroatomic Side-Chains" J. Comb. Chem. 2005, 7(6), 864-878. Lien - Article - Link

Fridkin, G.; Lubell, W. D. "Deazapurine solid-phase synthesis: combinatorial synthesis of a library of N3, N5, C6 trisubstituted pyrrolo[3,2-d]pyrimidine d erivatives on cross-linked polystyrene bearing a cysteamine linker" J. Comb. Chem. 2005, 7(6), 977-986. Lien - Article - Link

Rombouts, F. J. R.; Fridkin, G.; Lubell, W. D. "Deazapurine solid-phase synthesis: construction of 3-substituted pyrrolo[3,2-d]pyrimidine-6-carboxylates on cross-linked polystyrene bearing a cysteamine linker" J. Comb. Chem. 2005, 7(4), 589-598. Lien - Article - Link

Kaul, R.; Surprenant, S. Lubell, W. D. "Systematic Study of the Synthesis of Macrocyclic Dipeptide β-Turn Mimics Possessing 8-, 9- and 10- Membered Rings by Ring Closing Metathesis" J. Org. Chem. 2005, 70, 3838-3844 and addition/correction 2005, 70(12), 4901-4902. Lien - Article - Link and/et Lien - Correction - Link

Galaud, F.; Lubell, W. D. "Homoserine-Derived Cyclic Sulfamidate as Chiral Educt for The Diversity Oriented Synthesis of Lactam-Bridged Dipeptides" Biopolymers (Peptide Science) 2005, 80, 665-674. Lien - Article - Link

Sajjadi, Z.; Lubell, W. D. "Amino Acid-Azetidine Chimeras: Synthesis of Enantiopure 3-Substituted Azetidine-2-carboxylic Acids" J. Peptide Res. 2005, 65(2), 298-310. Lien - Article - Link

Dettwiler, J. E.; Lubell, W. D. "Synthesis and Application of L-N-Boc-N-methyl-β-hydroxyvaline in the Preparation of a Depsipeptide" Can. J. Chem. 2005, 83, 793-800. Lien - Article - Link

Bélec, L.; Blankenship, J.W.; Lubell, W.D. "Examination of Structural Characteristics of the Potent Oxytocin Antagonists [dPen1,Pen6]-OT and [dPen1,Pen6,5-tBuPro7]-OT by NMR, Raman, CD Spectroscopy and Molecular Modeling." J. Peptide Sci. 2005, 11, 365-378. Lien - Article - Link