Kleski, K. A.; Shi, M.; Lohman, M.; Hymel, G.; Gattoji, V.; Andreana, P. R. (2020) Synthesis of an Aminooxy Derivative of the GM3 Antigen and its Application in Oxime Ligation. The Journal of Organic Chemistry DOI.org/10.1021/acs.joc.0c00320
Hohol, R. E.; Arcure, H.; Witczak, Z.; Bielski, R.; Kirschbaum, K.; Andreana, P.; Mencer, D. E. (2018) One-Pot Synthesis of Carbohydrate exo-Cyclic Enones and Hemiketals with 6,8-Dioxabicyclo-[3.2.1]Octane Moieties. Serendipitous Formation of a Spironolactone when 2-Pyridinecarboxaldehyde is used as the Reactant. Part II Tetrahedron 74: 7303-7309.
Esmati, N.; Maddirala, A. R.; Hussein, N.; Amawi, H.; Tiwari, A. K.; Andreana, P. R. (2018) Efficient Syntheses and Anti-Cancer Activity of Xenortides A-D Including ent/epi-Stereoisomers Organic & Biomolecular Chemistry 16: 5332-5342.
Jeelani, R.; Jahanbakhsh, S.; Kohan-Ghadr, H.-R.; Thakur, M.; Khan, S.; Aldhaheri, S. R.; Yang, Z.; Andreana, P. R.; Morris, R.; Abu-Souda, H. M. (2017) Mesna (2-Mercaptoethane Sodium Sulfonate) Functions as a Regulator of Myeloperoxidase. Free Radical Biology and Medicine 110: 54–62.
Shi, M.; Kleski, K. A.; Trabbic, K. R.; Bourgault, J.-P.; Andreana, P. R. (2016) STn-PS A1 as an Entirely Carbohydrate Immunogen: Synthesis and Immunological Evaluation. Journal of the American Chemical Society 138: 14264-14272.
Ghosh, S.; Nishat, S.; Andreana, P. R. (2016) Synthesis of an Aminooxy Derivative of the Tetrasaccharide Repeating Unit of Streptococcus dysgalactiae 2023 Polysaccharide and a PS A1 Conjugate Vaccine. Journal of Organic Chemistry 81: 4475-4485.
Trabbic, K. R.; Bourgault, J.-P.; Shi, M.; Clark, M.; Andreana, P. R. (2016) Immunological Evaluation of the Entirely Carbohydrate-based Thomsen-Friedenreich - PS B Conjugate. Organic and Biomolecular Chemistry 14: 3350-3355.
Maddirala, A. R.; Andreana, P. R. (2016) Synthesis of
3-Substituted-2-Indolinones via a Multicomponent Coupling Isocyanide Dependent
Microwave-Assisted Intramolecular Transamidation Process. European Journal of Organic Chemistry
Santra, S.; Andreana, T. L.; Bourgault, J.- P.; Andreana, P. R. (2015) Convertible Isocyanides: Application in Small Molecule Synthesis, Carbohydrate Synthesis and Drug Discovery, in Domino and Rearrangement Reactions in Glycoscience; Witczak, Z.; Bielski, R., Eds.; John Wiley & Sons Publisher Production Department. ISBN: 9781119044208.
Jean-Paul Bourgault completes the total synthesis of naturally occurring herbicide Thaxtomin A in a single synthetic transformation using a facile, streamlined and efficient multicomponent one-pot process. For his efforts, Mr. Bourgault was granted the inside cover of OBC as illustrated here. Although Thaxtomin A had been synthesized previously, this short route hopes to provide a library of Thaxtomin A derivatives that will be used to probe the compound's mechanism of action as it is currently still unknown. One of the keys to Jean-Paul's strategy is that the by-product of this reaction is water which bodes well with Thaxtomin A's story of being Bio-Friendly.
In addition a modified version of this article was published on the Royal Society of Chemistry learn chemistry web site under the annotated article section. This resource is aimed at teaching undergraduate students how to understand and interpret key aspects of journal articles through clearly defined outlines which are rewritten by the authors specifically for the students. Please click here for more information!
MedChemComm Carbohydrate Themed Issue
A MedChemComm themed issue was guest edited by Profs Garneau-Tsodikova and Baasov highlighting recent advances in the glycosciences in its broad sense to drug discovery.
Trabbic and De Silva's paper appeared in this issue which you should check out!
OBC Cover Art
The evil and disguised tumor cell is elusive in nature. It avoids immune surveillance and can metastasize at will. The cover art for Bourgault's paper above, illustrated by artist Miss Rachel A. Bourgault, aims to capture the see-saw battle between what is known about the surface glycans on tumor cells and how to exploit them to unmask the cell's evil doing. One of those surface carbohydrates is the Thomsen-Friedenriech (TF) antigen which is an alpha-linked dissaccharide found in high density on human breast, colon, stomach, bladder, prostate and liver tumor cells. The paper provides a route for it's synthesis and a protocol for it's conjugation to a zwitterionic polysaccharide called PS A1 which can induce the highly sought after T-cell immune response in vaccine design and development.
Abu-Soud, H. M.; Maitra, D.; Shaeib, F.; Byun, J.; Abdulhamid, I.; Saed, G. M.; Diamond, M. P.; Andreana, P. R.; Pennathur, S. (2014) Disruption of Heme-Peptide Covalent Cross-Linking in Mammalian Peroxidases by Hypochlorous Acid Journal of Inorganic Biochemistry 140: 245-254.
Silva, R. A.; Appulage, D. K.; Pietraszkiewicz, H.; Bobbitt, K. R.; Media, J.; Shaw,
J.; Valeriote, F. A.; Andreana, P. R. (2012) The Entirely Carbohydrate Immunogen Tn-PS A1 Induces a Cancer Cell
Selective Immune Response and Cytokine IL-17. Cancer Immunology, Immunotherapy
Shaw, J.; Chen, B.; Bourgault, J. P.; Jiang, H.; Kumar, N.; Mishra, J.; Valeriote, F. A.; Media, J.; Bobbitt, K.; Pietraszkiewicz, H.; Edelstein, M.; Andreana, P. R. (2012) Synthesis and Biological Evaluation of Novel N-phenyl-5-carboxamidyl Isoxazoles as Potential Chemotherapeutic Agents for Colon Cancer. American Journal of Biomedical Sciences 4: 14-25.
Abu-Soud, H. M.; Maitra, D.; Byun, J.; Souza, C. E. A.; Banerjee, J.; Andreana, P. R.; Pennathur, S. (2012) The Reaction of HOCl and Cyanocobalamin: Corrin Destruction and the Liberation of Cyanogen Chloride. Free Radical Biology and Medicine 52: 616-625.
Santra, S.; Andreana, P. R. (2011) A Bioinspired Ugi/Michael/aza-Michael Cascade Reaction in Aqueous Media: Natural Product-Like Molecular Diversity. Angewandte Chemie International Edition 50: 9418-9422. Designated as Hot Paper.
Maitra, D.; Byun, J.; Andreana, P. R.; Abdulhamid, I.; Diamond, M. P.; Saed, G. M.; Pennathur, S.; Abu-Soud, S. M. (2011) Reaction of Hemoglobin with HOCl: Mechanism of Heme Destruction and Free Iron Release. Free Radical Biology and Medicine 51: 374-386.
Yatawara, A. K.; Tiruchinapally, G.; Bordenyuk, A. N.; Andreana, P. R.; Benderskii, A. V. (2009) Carbohydrate Surface Attachment Characterized by Sum Frequency Generation Spectroscopy. Langmuir 25: 1901-1904.
De Silva, R. A.; Santra, S.; Andreana, P. R. (2008) A Tandem One-Pot, Microwave-Assisted Synthesis of Regiochemically Differentiated 1,2,4,5-Tetrahydro-1,4-benzodiazepin-3-ones. Organic Letters 10: 4541-4544. Highlighted In: Organic Chemistry Portal (Org. Chem. Highlights) October 15, 2008.
Andreana, P. R.; McLellan, J. S.; Chen, Y.; Wang, P. G. (2002) Synthesis of 2,6-Dideoxysugars via Ring Closing Olefinic Metathesis. Organic Letters 4: 3875-3878. Hot Article Oct./02. Cited in C&EN News Dec. 23/02.
Chen, X.; Fang, J.; Zhang, J.; Andreana, P. R.; Shao, J.; Kowal, P.; Wang, P. G. (2001) Sugar Nucleotide Regeneration Beads (Superbeads): A Versatile Tool for Practical Synthesis of Oligosaccharides. Journal of the American Chemical Society 123: 2081-2082.
- Hou, Y. -C.; Chen, Y. -S.; Amro, N. A.; Wadu-Mesthrige, K.; Andreana, P. R.; Wang, P. G. (2000) Nano-Molar Scale Nitric Oxide Generation From Self-Assembled Monolayer Modified Gold Electrodes. Chemical Communication 19: 1831-1832. Editor’s Choice in Science, Oct. 13/00.
Fang, J. W.; Chen, X.; Zhang, W.; Wang, J. Q.; Andreana, P. R.; Wang, P. G. (1999) A Unique Chemoenzymatic Synthesis of alpha-Galactosyl Epitope Derivatives Containing Free Amino Groups: Efficient Separation and Further Manipulation. Journal of Organic Chemistry 64: 4089-4094.
Chen, X.; Andreana, P. R.; Wang, P. G. (1999) Carbohydrates in Transplantation. Current Opinion in Chemical Biology 3: 650-658.
Holland, H. L.; Turner, C. D.; Andreana, P. R.; Nguyen, D. (1999) Biotransformation of Organic Sulfides. Part 12. Conversion of Heterocyclic Sulfides to Chiral Sulfoxides by Helminthosporium sp NRRL 4671 and Mortierella isabellina ATCC 42613. Canadian Journal of Chemistry Revue Canadienne de Chimie 77: 463-471.
Patel, K.; Andreana, P. R. "Recent Advances in the Stereochemical Outcome of Multicomponent Reactions Involving Convertable Isocyanides" In Coupling and Decoupling of Diverse Molecular Units in Glycosciences pgs. 67-89. ACS Symposium Series, Edited by: Z. J. Witczak and R. Bielski. Springer, Cham, Switzerland, 2018.
Santra, S.; Andreana, T.; Bourgault, J.-P.; Andreana, P. R. "Convertible Isocyanides: Application in Small Molecule Synthesis, Carbohydrate Synthesis, and Drug Discovery" In Domino and Intramolecular Rearrangement Reactions as Advanced Synthetic Methods in Glycoscience pgs. 121-194. Edited by: Z. J. Witczak and R. Bielski. John Wiley & Sons, Inc. New York 2015