The Andreana Research Group
The Andreana Research Group
Carbohydrate-based Vaccines, Small Molecule Synthesis, Immunology, Immunotherapy
57.
Ghosh, S.; Trabbic, K. R.; Shi, M.; Nishat, S.; Eradi, P.; Kleski, K. A.; Andreana, P. R. (2020) Chemical Synthesis and Immunological Evaluation of Entirely Carbohydrate Conjugate Globo H-PS A1 Chemical Science, DOI: 10.1039/D0SC04595K.
56.
Trabbic, K. R.; Bourgault, J.-P.; Shi, M.; Kleski, K. A.; Andreana, P. R. (2020) Enhanced Immune Response Against the Thomsen-Friedenreich Tumor Antigen Using a Bivalent Entirely Carbohydrate Conjugate. Molecules 6: 1319-1333.
55.
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
54.
Hossain, F.; Nishat, S.; Ghosh, S.; Boga, S.; Hymel, G. T.; Andreana, P. R. (2020) Synthesis of Glycoimmunogen Tn-Thr-PS A1 via Hydrazone Bond and Stability Optimization of PS A1 Monosaccharide Mimics Under Vaccine Development Conditions. Journal of Carbohydrate Chemistry 39: 107-129.
53.
Kleski, K. A.; Andreana, P. R. (2019) Developments in CRM197 Glycoconjugates for Anticancer Vaccines. American Journal of Biomedical Science & Research 6: 212-215.
52.
Hossain, F.; Andreana, P. R. (2019) Developments in Carbohydrate-Based Cancer Therapeutics. Pharmaceuticals 12: 84-102.
51.
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.
50.
Eradi, P.; Ghosh, S.; Andreana, P. R. (2018) Total Synthesis of Zwitterionic Tetrasaccharide Repeating Unit from Bacteroides fragilis ATCC 25285/NCTC 9343 Capsular Polysaccharide PS A1 with Alternating Charges on Adjacent Monosaccharides. Organic Letters 20: 4526–4530.
49.
Trabbic, K. R.; Kleski, K. A.; Shi, M.; Bourgault, J.-P.; Prendergast, J. M.; Dransfield, D. T.; Andreana, P. R. (2018) Production of a Mouse Monoclonal IgM Antibody that Targets the Carbohydrate Thomsen-nouveau Cancer Antigen Resulting in in vivo and in vitro Tumor Killing. Cancer Immunology, Immunotherapy 67: 1437-1447.
48.
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.
47.
Maddirala, A. R.; Andreana, P. R. (2018) Methyl Isocyanide as a Convertible Functional Group for the Synthesis of Spirocyclic Oxindole γ–Lactams via Post Ugi-4CR/Transamidation/Cyclization in a One-Pot Three Step Sequence. Beilstein Journal of Organic Chemistry 14: 875–883.
46.
Patel, K.; Song, F.; Andreana, P. R. (2017) Synthesis of Substrate Analogues as Potential Inhibitors for Mycobacterium tuberculosis enzyme MshC. Carbohydrate Research 453-454: 10-18.
45.
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.
44.
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.
43.
Nishat, S.; Andreana, P. R. (2016) Entirely Carbohydrate-based Vaccines: An Emerging Field for Specific and Selective Immune Responses. Vaccines 4: 19.
42.
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.
41.
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.
40.
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
39.
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.
38.
Ghosh, S.; Andreana, P. R. (2015) Di-t-butylsilyl Bis(trifluoromethanesulfonate). e-EROS Encyclopedia of Reagents for Organic Synthesis March 11. See .pdf here.
37.
Shaik, A. A.; Nishat, S.; Andreana, P. R. (2015) Stereoselective Synthesis of Natural and Non-natural Thomsen-nouveau Antigens and Hydrazide Derivatives. Organic Letters 17: 2582−2585.
36.
Bourgault, J. P.; Maddirala, A.; Andreana, P. R. (2014) A One-Pot Multicomponent Coupling/Cyclization for Natural Product Herbicide (±)-Thaxtomin A. Organic and Biomolecular Chemistry 12: 8125-8127.
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!
35.
Ghosh, S.; Andreana, P. R. (2014) Synthesis of an Aminooxy Derivative of the Trisaccharide Globotriose Gb3. Journal of Carbohydrate Chemistry 33: 381-394.
34.
Trabbic, K. R.; De Silva, R. A; Andreana, P. R. (2014) Elucidating Structural Features of an Entirely Carbohydrate Cancer Vaccine Construct Employing Circular Dichroism and Fluorescent Labeling. Medicinal Chemistry Communication, 5: 1143-1149.
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!
33.
Bourgault, J. P.; Trabbic, K. R.; Shi, M.; Andreana, P. R. (2014) Synthesis of the Tumor Associative α-Aminooxy Disaccharide of the TF Antigen and its Conjugation to a Polysaccharide Immune Stimulant. Organic and Biomolecular Chemistry, 12: 1699-1702.
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.
32.
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.
31.
De 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 61: 581-585.
30.
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.
29.
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.
28.
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.
27.
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.
26.
Maitra, D.; Byun, J.; Andreana, P. R.; Abdulhamid, I.; Saed, G. M.; Diamond, M. P.; Pennathur, S.; Abu-Soud, S. M. (2011) Mechanism of Hypochlorous Acid-Mediated Heme Destruction and Free Iron Release. Free Radical Biology and Medicine 51: 364-373.
25.
Santra, S.; Jonas, E.; Bourgault J.-P.; El-Baba, T; Andreana, P. R. (2011) Kinetic Products Under Thermal Conditions: Rapid Entry into Anomeric Substituted a/b-D-Galactofuranosides Using Microwave Irradiation and Selective Lewis Acids. Journal of Carbohydrate Chemistry 30: 27-40.
24.
Santra, S.; Andreana, P. R. (2011) A Rapid, One-Pot, Microwave-Influenced Synthesis of Spiro-2,5-Dikopiperazines via a Cascade Ugi/6-exo-trig aza-Michael Reaction. Journal of Organic Chemistry 76: 2261-2264.
23.
De Silva, R. A.; Wang, Q.; Chidley, T.; Appulage, D. K.; Andreana, P. R. (2009) Immunological Response from an Entirely Carbohydrate Antigen: Design of Synthetic Vaccines Based on Tn-PS A1 Conjugates. Journal of the American Chemical Society 131: 9622-9623.
23.
De Silva, R. A.; Wang, Q.; Chidley, T.; Appulage, D. K.; Andreana, P. R. (2009) Immunological Response from an Entirely Carbohydrate Antigen: Design of Synthetic Vaccines Based on Tn-PS A1 Conjugates. Journal of the American Chemical Society 131: 9622-9623.
23.
De Silva, R. A.; Wang, Q.; Chidley, T.; Appulage, D. K.; Andreana, P. R. (2009) Immunological Response from an Entirely Carbohydrate Antigen: Design of Synthetic Vaccines Based on Tn-PS A1 Conjugates. Journal of the American Chemical Society 131: 9622-9623.
23.
De Silva, R. A.; Wang, Q.; Chidley, T.; Appulage, D. K.; Andreana, P. R. (2009) Immunological Response from an Entirely Carbohydrate Antigen: Design of Synthetic Vaccines Based on Tn-PS A1 Conjugates. Journal of the American Chemical Society 131: 9622-9623.
22.
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.
21.
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.
20.
Santra, S.; Andreana, P. R. (2007) A One-Pot, Microwave-Influenced Synthesis of Diverse Small Molecules by Multicomponent Reaction Cascades. Organic Letters 9: 5035-5038. Highlighted In: Organic Chemistry Portal (Org. Chem. Highlights) November 15, 2007.
19.
Andreana, P. R.; Liu, C. C.; Schreiber, S. L. (2004) Stereochemical Control of the Passerini Reaction. Organic Letters 6: 4231-4233.
18.
Andreana, P. R.; Kowal, P.; Janczuk, A. J.; Wang, P. G. (2004) Alpha-Galactosyl Trisaccharide Epitope: Modification of the 6-Primary Positions and Recognition by Human Anti-alpha-Gal Antibody. Glycoconjugate Journal 20: 107-118.
17.
Sello, J. K.; Andreana, P. R.; Lee, D.; Schreiber, S. L. (2003) Stereochemical Control of Skeletal Diversity. Organic Letters 5: 4125-4127.
16.
Postema, M. H. D.; Piper, J. L.; Liu, L.; Shen, J.; Faust, M.; Andreana, P. (2003) Synthesis and Partial Biological Evaluation of a Small Library of Differentially-Linked -C-Disaccharides. Journal of Organic Chemistry 68: 4748-4754.
15.
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.
14.
Andreana, P. R.; Sanders, T.; Janczuk, A.; Warrick, J. I.; Wang, P. G. (2002) Chemo-Enzymatic Synthesis of Polyhydroxyazepanes. Tetrahedron Letters 43: 6525-6528.
13.
Janczuk, A. J.; Zhang, W.; Andreana, P. R.; Warrick, J.; Wang P. G. (2002) The Synthesis of Deoxy alpha-Gal Epitope Derivatives for the Evaluation of Anti-alpha-Gal Antibody Binding. Carbohydrate Research 337: 1247-1259.
12.
Andreana, P. R.; Xie, W.; Cheng, H. N.; Qiao, L.; Murphy, D. J.; Gu, Q. M.; Wang, P. G. (2002) In-Situ Preparation of beta-D-1-O-Hydroxylamino Carbohydrate Polymers Mediated by Galactose Oxidase. Organic Letters 4: 1863-1866.
11.
Zhang, J.; Kowal, P.; Fang, J.; Andreana, P.; Wang, P. G. (2002) Efficient Chemoenzymatic Synthesis of Globotriose and Its Derivatives with a Recombinant alpha-(1-4)-Galactosyltransferase. Carbohydrate Research 337: 969-976.
10.
Chen, X.; Zhang, J.; Kowal, P.; Liu, Z.; Andreana, P. R.; Lu, Y.; Wang, P. G. (2001) Transferring a Biosynthetic Cycle into a Productive Escherichia coli Strain: Large-Scale Synthesis of Galactosides. Journal of the American Chemical Society 123: 8866-8867.
9.
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.
8.
Holland, H. L.; Andreana, P. R.; Salehzadeh-Asl, R.; van Vliet, A.; Ihasz, N. J.; Brown, F. M. (2000) Beauveria bassiana ATCC 7159 Contains an L-Specific alpha-Amino Acid Benzamidase. Monatshefte fur Chemie 131: 667-672.
7.
1. 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.
6.
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.
5.
Chen, X.; Andreana, P. R.; Wang, P. G. (1999) Carbohydrates in Transplantation. Current Opinion in Chemical Biology 3: 650-658.
4.
Hou, Y.-C.; Wang, J.-Q.; Andreana, P. R.; Cantauria, G.; Tarasia, S.; Sharp, L.; Braunschweiger, P. G.; Wang, P. G. (1999) Targeting Nitric Oxide to Cancer Cells: Cytotoxicity Studies of Glyco-S Nitrosothiols. Bioorganic and Medicinal Chemistry Letters 9: 2255-2258.
3.
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.
2.
Holland, H. L.; Andreana, P. R.; Brown, F. M. (1999) Biocatalytic and Chemical Routes to all the Stereoisomers of Methionine and Ethionine Sulfoxides. Tetrahedron: Asymmetry 10: 2833-2843.
1.
Holland, H. L.; Kohl, A.; Larsen, B. G.; Andreana, P.; Gu, J. X. (1997) Preparation of Substituted (R)-2-Alkanols by Microbial Hydroxylation. Journal of Molecular Catalysis B-Enzymatic. 2: L253-L255.
4.
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.
3.
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
2.
Andreana, P. R.; Xie, W.; Wang, P. G. “Synthesis and Modifications of Carbohydrates Through Biotechnology” In Biocatalysis in Polymer Science pgs. 188-202. ACS Symposium Series, Edited by: R. Gross and H.N. Cheng. ACS Books, Washington DC, 2003.
1.
Andreana, P. R.; Zhang, W.; Wang, P. G. “From a Carbohydrate Sequence to Extensive Research Programs, the alpha-Gal Epitope as a Case Study” In Glycochemistry: Principles, Synthesis, and Applications pgs. 581-624. Edited by: P.G. Wang and C. Bertozzi. Marcel Dekker, Inc. New York, 2001.