Refereed Journal Publications & Reviews

2014

 

152. Bourguet, C.B.; Claing, A.; Laporte, S.; Hébert, T.E.; Chemtob, S.; Lubell, W.D. "Synthesis of azabicycloalkanone amino acid and aza-peptide mimics, and their application as modulators of the prostaglandin-F2α receptor for delaying preterm birth" Can. J. Chem., 2014, 92 (11), 1031-1040. https://doi.org/10.1139/cjc-2014-0289

 

151. Traoré, M.; Doan, N.-D.; Lubell, W. D. "Diversity-Oriented Synthesis of Azapeptides with Basic Amino Acid Residues: Aza-Lysine, Aza-Ornithine and Aza-Arginine" Org. Lett., 2014, 16 (13), 3588–3591. DOI: 10.1021/ol501586y

 

150. Bourguet, C. B.; Boulay, P.-L.; Claing, A.; Lubell, W. D. “Design and synthesis of novel azapeptide activators of apoptosis mediated by caspase-9 in cancer cells" Bioorg. Med. Chem. Lett. 2014, 24 (15), 3361–3365. https://doi.org/10.1016/j.bmcl.2014.05.095

 

149. Doan, N.-D.; Hopewell, R.; Lubell, W. D. “N-Aminoimidazolidin-2-one Peptidomimetics” Org. Lett., 2014, 16 (8), 2232–2235.

DOI: 10.1021/ol500739k

 

148. Zhang, J.; Proulx, C.; Tomberg, A.; Lubell, W.D. “Multicomponent Diversity-Oriented Synthesis of Aza-Lysine-Peptide Mimics” Org. Lett., 2014, 16 (8), 298–301. DOI: 10.1021/ol403297v

 

147. Dörr, A. A.; Lubell, W.D. “Aminophenylpyrrole synthesis and application to pyrrolo[1,2-c]quinazolinone synthesis” Heterocycles 2014, 88 (2), 1149-1161, Victor Snieckus's Special Issue. DOI: 10.3987/COM-13-S(S)73

 

146. Proulx, C.; Lubell, W. D., “Analysis of N-amino-imidazolin-2-one peptide turn mimic 4-position substituent effects on conformation by X-ray crystallography.” Biopolymers, Peptide Science, 2014, 102 (1), 7-15. DOI: 10.1002/bip.22327

 

145. Saroukou, M.S.M.; Skalski, T.; Skene, W. G.; Lubell, W. D. “Conjugated C3 symmetric aryl tripyrroles and aryl bipyrroles:  synthesis, optical and electronic properties” Tetrahedron 2014, 70, 450–458. https://doi.org/10.1016/j.tet.2013.11.043

 

144. Khashper, A.; Lubell, W. D. “Design, synthesis, conformational analysis and application of indolizidin-2-one dipeptide mimics” Org. Biomol. Chem. 2014, 12, 5052-5070. DOI: 10.1039/C4OB00777H

 

2013

 

143. Bouayad-Gervais, S. H.; Lubell, W. D. “Examination of the Potential for Adaptive Chirality of the Nitrogen Chiral Center in Aza-Aspartame” Molecules 2013, 18, 14739-14746. doi:10.3390/molecules181214739

 

142. Garcia-Ramos, Y.; Lubell, W., D. “Synthesis and alkylation of aza-glycinyl dipeptide building blocks” J. Peptide Sci. 2013, 19 (12), 725-729.

DOI: 10.1002/psc.2572

 

141. Rivera, J.-C.; Sitaras, N.; Noueihed, B.; Hamel, D.; Madaan, A.; Zhou, T.; Honoré, J.-C.; Quiniou, C.; Joyal, J.-S.; Hardy, P.; Sennlaub, F.; Lubell, W.; Chemtob, S. “Microglia and IL-1β in ishchemic retinopathy elicit microvascular degeneration through neuronal semaphoring 3A” Arteriosclerosis, Thrombosis, and Vascular Biology, 2013, 33, 1881-1891. https://doi.org/10.1161/ATVBAHA.113.301331

 

140. Leduc M, Hou X, Hamel D, Sanchez M, Honoré J-C, Lubell W, Varma DR, Mancini J, Peri KG, Heveker N, Chemtob S. “Restoration of renal function by a novel prostaglandin EP4 receptor-derived peptide in models of acute renal failure.” Am. J. Physiol. Regul. Integr. Comp. Physiol. 304:R10-R22, 2013doi:  10.1152/ajpregu.00138.2012

 

139. Jamieson, A. G.; Sabatino, D.; Boutard, N.;  Lubell, W. D. “Peptide Scanning for Studying Structure-Activity Relationships in Drug Discovery” Chem. Bio. Drug Design 2013, 81, 148-165. DOI: 10.1111/cbdd.12042

 

2012

 

138. Garcia-Ramos, Y.; Proulx, C.; Lubell, W., D. “Synthesis of hydrazine and azapeptide derivatives by alkylation of carbazates and semicarbazones” Can. J. Chem., 2012, 90, 985-993. https://doi.org/10.1139/v2012-070

 

137. Proulx, C.; Lubell, W., D. “N-Amino-imidazolin-2-one Peptide Mimic Synthesis and Conformational Analysis” Org. Lett., 2012, 14, 4552–4555.  DOI: 10.1021/ol302021n

 

136. Quiniou C, Goupil E, Lubell W, Laporte S, Chemtob S. “Découver te de modulateurs allostériques  peptidiques de récepteurs  transmembranaires: focus sur la sélectivité fonctionnelle” Médecine Sci. Am. 1:123-138, 2012. http://s3.amazonaws.com/msamerique/documents/52/original/MSA2012-07%20.pdf?1342038798

 

135. Proulx, C.; Picard, E.; Boeglin, B.; Pohankova,  P.; Chemtob,  S.; Ong,  H.; Lubell,  W.,  D. “Azapeptide Analogues of GHRP-6 as Cluster of Differentiation 36 Receptor Ligands with Reduced Affinity for the Growth Hormone Secretagogue Receptor 1a.” J. Med. Chem. 2012, 55, 6502–6511. DOI: 10.1021/jm300557t

 

134. Dörr, A. A.; Lubell, W.D. “Synthesis of Protected 2-Pyrrolylalanine for Peptide Chemistry and Examination of Its Influence on Prolyl Amide Isomer Equilibrium” J. Org. Chem. 2012, 77, 6414–6422.  DOI: 10.1021/jo3005809

 

133. Spiegel, J.; Mas-Moruno, C.; Kessler, H.; Lubell, W.D. "Cyclic aza-peptide integrin ligand synthesis and biological activity" J. Org. Chem. 2012, 77, 5271–5278.  DOI: 10.1021/jo300311q

 

132. Gnaccarini, C.; Ben-Tahar, W.; Mulani, A.; Roy, I.; Lubell, W.D.; Pelletier, J.N.; Keillor, J.W. "Site-specific protein propargylation using tissue transglutaminase" Org. Biomol. Chem., 2012, 10, 5258-5265. http://dx.doi.org/10.1039/C2OB25752A

 

131. Turcotte, S.; Bouayad-Gervais, S.H.; Lubell, W.D. “N-Aminosulfamide Peptide Mimic Synthesis by Alkylation of Aza-sulfurylglycinyl Peptides” Org. Lett. 2012, 14, 1318–1321. DOI: 10.1021/ol3001987

 

2011

 

130. Tshibaka, T.; Bishop, S.; Roche, I.U.; Dufresne, S.; Lubell, W.D.; Skene, W.G. “Conjugated 4-methoxybipyrrole thiophene azomethines: synthesis, opto-electronic properties and crystallographic characterization” Chem. Eur. J. 2011, 17, 10879 – 10888.

 

129. Bourguet, C.; Goupil, E.; Tassy, D.; Hou, W.; Thouin, E.; Polyak, F.; Hebert, T. E.; Claing, A.; Laporte, S. A. ; Chemtob, S.; Lubell, W. D. "Targeting the Prostaglandin F2α Receptor for Preventing Preterm Labor with Azapeptide Tocolytics" J. Med. Chem. 2011, 54, 6085–6097.

 

128. Sabatino, D., Proulx, C., Pohankova, P., Ong, H., Lubell, W.D.  “Structure-Activity Relationships of GHRP-6 Azapeptide Ligands of the CD36 Scavenger Receptor by Solid-Phase Submonomer Azapeptide Synthesis ” J. Am. Chem. Soc. 2011, 133, 12493–12506.

 

127. Godina, T. A.; Lubell, W. D. “Mimics of Peptide Turn Backbone and Side-Chain Geometry by a General Approach for Modifying Azabicyclo[5.3.0]alkanone Amino Acids” J. Org. Chem. 2011, 76, 5846–5849.

       

126. Bolduc, O. R.; Lambert-Lanteigne, P.; Colin, D. Y.; Zhao, S.S; Proulx, C.; Boeglin, D.; Lubell, W. D.; Pelletier, J. N.; Féthière, J.; Ong, H.; Masson, J.-F. “Modified peptide monolayer binding His-tagged biomolecules for small ligand screening with SPR biosensors” Analyst, 2011 136, 3142-3148.

 

125. Boutard, N.; Dufour-Gallant, J.; Deaudelin, P.; Lubell, W.D. “Pyrrolo[3,2-e][1,4]diazepin-2-one Synthesis: A Head-to-Head Comparison of Soluble versus Insoluble Supports” J. Org. Chem. 2011, 76, 4533–4545.

 

124. Proulx, C.; Sabatino, D.; Hopewell, R.; Spiegel, J.; García-Ramos, Y.; Lubell, W.D. “Azapeptides and their therapeutic potential: current issues and new possibilities” Future Med. Chem. 2011, 1139–1164. doi: 10.4155/fmc.11.74

 

123. Boutard, N.; Turcotte, S.; Beauregard, K.; Quiniou, C.; Chemtob, S. Lubell, W.D. “Examination of the Active Secondary Structure of the Peptide APG-101.10, an Allosteric Modulator of the Interleukin-1 Receptor, by Positional Scanning Using b-Amino g-Lactams” J. Peptide Sci. 2011, 17, 288–296.

 

122. Dörr, A. A.; Lubell, W. D. “Synthesis and peptide coupling of protected 2-pyrrolylalanine” Tetrahedron Letters 2011, 52, 2159-2161.

 

2010

 

121. Picard, E.; Houssier, M.; Bujold, K.; Sapieha, P.; Lubell, W.; Dorfman, A.; Racine, J.; Hardy, P.; Febbraio, M.; Lachapelle, P.; Ong, H.; Sennlaub, F.; Chemtob, S. “CD36 plays an important role in the clearance of oxLDL and associated age-dependent sub-retinal deposit.” Aging 2010, 12, 981-9.

 

120. St-Cyr, D. J.; Maris, T.; Lubell, W. D. “Conformational analysis of hydroxylactam dipeptides as constrained Ser/Thr peptide mimics.” Heterocycles 2010, 82, 729-737.

 

119. Proulx, C.; Lubell, W. D. “Aza-1,2,3-triazole-3-alanine Synthesis via Copper-catalyzed 1,3-Dipolar Cycloaddition on Aza-progargylglycine” J. Org. Chem. 2010, 75, 5385-5387.

 

118. Proulx, C.; Lubell, W. D.  "Copper-Catalyzed N-Arylation of Semicarbazones for the Synthesis of Aza-arylglycine-Containing Aza-Peptides" Org. Lett. 2010, 12, 2916-2919.

 

117. Kassem, T.; Zhu, X.X.; Lubell, W.D. “Poly(vinyl alcohol)-graft-poly(ethylene glycol)-supported hydroxyproline catalysis of stereoselective aldol reactions" Macromol. Symp. 2010, 297, 101-107.

 

116. Goupil, E.; Tassy, D.; Bourguet, C.; Quiniou, C.; Wisehart, V.; Pétrin, D.; Le Gouill, C.; Devost, D.; Zingg, H. H.; Bouvier, M.; Saragovi, H. U.; Chemtob, S.; Lubell, W. D.; Claing, A.; Hebert, T. E.; Laporte, S. A. “­A novel biased allosteric compound inhibitor of parturition, selectively impedes the PGF2a-mediated Rho/Rock signaling pathway” J. Biol. Chem. 2010, 285, 25624-25636.

 

115. Bourguet, C.B.; Sabatino, D.; Proulx, C.; Klocek, S.; Lubell, W.D. " Solution-phase sub-monomer diversification of aza-dipeptide building blocks and their application in aza-peptide and aza-diketopiperazine synthesis.” J. Peptide Sci. 2010, 16, 284-296.

 

114. St.-Cyr, D.; Jamieson, A. G.; Lubell, W.D. "α-Amino-β-hydroxy-γ-lactams, constrained serine and threonine dipeptide mimics" Org. Lett. 2010, 12 (8), 1652–1655.

 

113. Tong, W.; Gagnon, M.; Sprules, T.; Gilbert, M.; Chowdhury, S.; Meerovitch, K.; Hansford, K.; Purisima, E. O.; Blankenship, J. W.; Cheung, N.-K. V.; Gehring, K.; Lubell, W. D.; Saragovi, H. U.; "Small Molecule Ligands of GD2 Ganglioside, Designed from NMR Studies, Exhibit Induced-Fit Binding and Bioactivity." Chemistry & Biology, 2010, 17 (2), 183-194.

 

112. Ronga, L.; Jamieson, A. G.; Beauregard, K.; Quiniou, C.; Chemtob, S.; Lubell, W.D. "Insertion of Multiple alpha-Amino gamma-Lactam (Agl) Residues into a Peptide Sequence By Solid-Phase Synthesis on SynPhase Lanterns” Biopolymers, Peptide Science 2010, 94 (2), 183 - 191.

 

111. Boutard, N.; Jamieson, A. G.; Ong, H.; Lubell, W.D. "Structure-Activity Analysis of the Growth Hormone Secretagogue GHRP-6 by α− and β−Amino γ−Lactam Positional Scanning" Chemical Biology and Drug Design 2010, 75 (1), 40-50.

 

20. Beausoleil, E.; Sharma, R.; Michnick, S.; Lubell, W. D. "Alkyl 3-Position Substituents Retard the Isomerization of Prolyl and Hydroxyprolyl amides in water". J. Org. Chem. 1998, 63, 6572-8.

 

19. Polyak, F.; Lubell, W. D. "Rigid Dipeptide Mimics: Synthesis of Enantiopure 5- and 7-Benzyl, and 5,7-Dibenzyl Indolizidinone Amino Acids Via Enolization and Alkylation of d-Oxo a,w-Di-[N-(9-(9-phenylfluorenyl))amino]azelate Esters." J. Org. Chem. 1998, 63, 5937-5949.

 

1997

18. Hanessian, S.; Mcnaughtonsmith, G; Lombart, H.-G.; Lubell, W. D. "Design and Synthesis of Conformationally Constrained Amino Acids as Versatile Scaffolds and Peptide Mimetics". Tetrahedron 1997, 53, 12789-12854.

 

1996

17. Lombart, H.-G.; Lubell, W. D. "Rigid Dipeptide Mimetics.  Efficient Synthesis of Enantiopure Indolizidinone Amino Acids". J. Org. Chem. 1996, 61, 9437-9446.

 

16. Beausoleil, E.; l'Archevêque, B.; Bélec, L.; Atfani, M.; Lubell, W. D. "5-tert-Butylproline". J. Org. Chem. 1996, 61, 9447-9454.

 

15. Beausoleil, E.; Lubell, W. D. "Steric Effects on the Amide Isomer Equilibrium of Prolyl Peptides. Synthesis & Conformational Analysis of N-Ac-5-tert-Butylproline N'-Methylamides". J. Am. Chem. Soc. 1996, 118, 12902-12908.

 

14. Gosselin, F.; Di Renzo, M.; Ellis, T. Lubell, W. D. "Photoacoustic FT-IR, A Non-Destructive Method for Sensitive Spectroscopic Analysis of Solid-Phase Org. Chem.". J. Org. Chem. 1996, 61, 7980-7981

 

13. Sharma, R.; Lubell, W. D. "Regioselective Enolization and Alkylation of 4-Oxo-N-(9-phenylfluoren-9-yl)proline: Synthesis of Enantiopure Proline-Valine and Hydroxyproline-Valine Chimeras". J. Org. Chem. 1996, 61, 202-209.

 

1995

12. Gill, P.; Lubell, W. D. "Synthesis of Enantiopure Arylkainoids; Preparation of (2S)-∆3-4-Phenylkainic Acid". J. Org. Chem. 1995, 60, 2658-2659.

 

11. Atfani, M.; Lubell, W. D. "Synthesis of (S)-2-Amino-3-(3-tert-butyl-4-isoxazol-5(2H)-one)propionic acid". J. Org. Chem. 1995, 60, 3184-3188.

 

10. Kitamura, M.; Tokunaga, M.; Pham, P.; Lubell, W. D.; Noyori, R. "Asymmetric Synthesis of a-Amino b-Hydroxy Phosphonic Acids Via BINAP–Ruthenium Catalyzed Hydrogenation". Tetrahedron Lett. 1995, 36, 5769-5772.

1994

9. Lombart, H.-G.; Lubell, W. D. "Synthesis of Enantiopure a,w-Diamino Dicarboxylates and Azabicycloalkane Amino Acids by Claisen Condensation of a-N-(phenylfluorenyl)amino Dicarboxylates". J. Org. Chem. 1994, 59, 6147-6149.

 

8. Pham, T.; Lubell, W. D. "A Practical Enantioselective Synthesis of a-Aminodicarboxylates.  Preparation of D- and L-a-Aminoadipate, a-Aminopimelate, and a-Aminosuberate". J. Org. Chem. 1994, 59, 3676 - 3680.

 

1993

7. Ibrahim, H. H.; Lubell, W. D. "Synthesis of Enantiopure d-Oxo a-Amino Esters and Prolines Via Acylation of N-Phenylfluorenylglutamate Enolates". J. Org. Chem. 1993, 58, 6438 - 6441.

1992

6. Jamison, T. F.; Lubell, W. D.; Dener, J. M.; Krisché, M. J.; Rapoport, H. "Synthesis of 9-Bromo-9-phenylfluorene". Org. Syn. 1992, 71, 220 - 235.

1991

5. Lubell, W. D.; Kitamura, M.; Noyori, R. "Enantioselective Synthesis of b-Amino Acids Based on binap – Ruthenium(II) Catalyzed Hydrogenation". Tetrahedron: Asymm. 1991, 2, 543-554.

 

1990

4. Lubell, W. D.; Jamison, T. F.; Rapoport, H. "N-(9-Phenylfluoren-9-yl)a-Amino Ketones and a-Amino Aldehydes as Chiral Educts for the Synthesis of Optically Pure 4-Alkyl 3-Hydroxy 2-Amino Acids.  Synthesis of the C-9 Amino Acid, MeBmt, Present in Cyclosporin".  J. Org. Chem. 1990, 55, 3511-3522. 

 

1989

3. Lubell, W. D.; Rapoport, H. "Surrogates for Chiral Aminomalondialdehyde.  Synthesis of N-(9-Phenylfluoren-9-yl)serinal and N-(9-Phenylfluoren-9-yl)vinylglycinal". J. Org. Chem. 1989, 54, 3824-3831. 

 

1988

2. Lubell, W. D.; Rapoport, H. "a-Amino Acids as Chiral Educts for Asymmetric Products.  Alkylation of N-Phenylfluorenyl a-Amino Ketones.  Synthesis of a-Alkyl Substituted Carboxylic Acids". J. Am. Chem. Soc. 1988, 110, 7447-7455. 

 

1987

1. Lubell, W. D.; Rapoport, H.  "Configurational Stability of N-Protected a-Amino Aldehydes ". J. Am. Chem. Soc. 1987, 109, 236-239.