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Journal of Carbohydrate Chemistry Volume 24, 2005 - Issue 4-6

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Original Articles

Highly Efficient Stereospecific Preparation of Tn and TF Building Blocks Using Thioglycosyl Donors and the Ph₂SO/Tf₂O Promotor SystemFootnote*
* Dedicated to the memory of Professor Jacques H. van Boom

David Cato Complex Carbohydrate Research Center, University of Georgia, Athens, Georgia, USA

Therese Buskas Complex Carbohydrate Research Center, University of Georgia, Athens, Georgia, USA

Geert‐Jan Boons Complex Carbohydrate Research Center, University of Georgia, Athens, Georgia, USACorrespondence[email protected]

Pages 503-516 | Received 22 Feb 2005, Accepted 04 Apr 2005, Published online: 16 Aug 2006

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Yashapal Singh, Scott A. Geringer & Alexei V. Demchenko. (2022) Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century. Chemical Reviews 122:13, pages 11701-11758.
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Bhaswati Ghosh, Nabarupa Bhattacharjee, Ananda Rao Podilapu, Krishna Puri & Suvarn S. Kulkarni. (2022) Total Synthesis of the Repeating Units of O -Specific Polysaccharide of Pseudomonas chlororaphis subsp. aureofaciens UCM B-306 via One-Pot Glycosylation . Organic Letters 24:20, pages 3696-3701.
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Shuaishuai Wang, Congcong Chen, Madhusudhan Reddy Gadi, Varma Saikam, Ding Liu, He Zhu, Roni Bollag, Kebin Liu, Xi Chen, Fengshan Wang, Peng George Wang, Peixue Ling, Wanyi Guan & Lei Li. (2021) Chemoenzymatic modular assembly of O-GalNAc glycans for functional glycomics. Nature Communications 12:1.
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Matteo Panza, Salvatore G. Pistorio, Keith J. Stine & Alexei V. Demchenko. (2018) Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges. Chemical Reviews 118:17, pages 8105-8150.
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Maqbool A. Siddiqui, Shailesh Ambre, Susan K. Keay, Jeffrey M. Rhyne, Chen-Ou Zhang & Joseph J. BarchiJr.Jr.. (2017) Glycoamino Acid Analogues of the Thomsen–Friedenreich Tumor-Associated Carbohydrate Antigen: Synthesis and Evaluation of Novel Antiproliferative Factor Glycopeptides. ACS Omega 2:9, pages 5618-5632.
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Seyed I. Sadraei, Michael R. Reynolds & John F. Trant. 2017. 137 237 .

Jordan D. Lewicky, Marina Ulanova & Zi-Hua Jiang. (2016) Synthesis of a TLR4 Agonist-Carbohydrate Antigen Conjugate As A Self-Adjuvanting Cancer Vaccine. ChemistrySelect 1:5, pages 906-910.
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Martin A. Fascione, Robin Brabham & W. Bruce Turnbull. (2016) Mechanistic Investigations into the Application of Sulfoxides in Carbohydrate Synthesis. Chemistry - A European Journal 22:12, pages 3916-3928.
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Kelly N. Chuh, Anna R. Batt & Matthew R. Pratt. (2016) Chemical Methods for Encoding and Decoding of Posttranslational Modifications. Cell Chemical Biology 23:1, pages 86-107.
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Ryoichi Arihara, Kosuke Kakita, Noritoshi Suzuki, Seiichi Nakamura & Shunichi Hashimoto. (2015) Glycosylation with 2-Acetamido-2-deoxyglycosyl Donors at a Low Temperature: Scope of the Non-Oxazoline Method. The Journal of Organic Chemistry 80:9, pages 4259-4277.
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Fei Yu, Matthew S. McConnell & Hien M. Nguyen. (2015) Scalable Synthesis of Fmoc-Protected GalNAc-Threonine Amino Acid and T N Antigen via Nickel Catalysis . Organic Letters 17:8, pages 2018-2021.
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Santanu Jana, Madhu Emmadi & Suvarn S. Kulkarni. (2015) First Synthesis of the α- L -Serine Linked Consensus Disaccharide of Neisseria gonorrhoeae and Neisseria meningitidis . Israel Journal of Chemistry 55:3-4, pages 398-402.
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Madhu Emmadi & Suvarn S. Kulkarni. (2014) Total synthesis of the bacillosamine containing α-l-serine linked trisaccharide of Neisseria meningitidis. Carbohydrate Research 399, pages 57-63.
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Christian Pett & Ulrika Westerlind. (2014) A Convergent Strategy for the Synthesis of Type‐1 Elongated Mucin Cores 1–3 and the Corresponding Glycopeptides. Chemistry – A European Journal 20:24, pages 7287-7299.
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Jean Paul Bourgault, Kevin R. Trabbic, Mengchao Shi & Peter R. Andreana. (2014) Synthesis of the tumor associative α-aminooxy disaccharide of the TF antigen and its conjugation to a polysaccharide immune stimulant. Org. Biomol. Chem. 12:11, pages 1699-1702.
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M. Fiore, B. Thomas, P. Dumy & O. Renaudet. 2013. Biomaterials for Cancer Therapeutics. Biomaterials for Cancer Therapeutics 59 94 .

Madhu Emmadi & Suvarn S. Kulkarni. (2013) Orthogonally protected d-galactosamine thioglycoside building blocks via highly regioselective, double serial and double parallel inversions of β-d-thiomannoside. Organic & Biomolecular Chemistry 11:29, pages 4825.
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Masanori Tayu, Kazuhiro Higuchi, Masato Inaba & Tomomi Kawasaki. (2013) Sulfoxide-TFAA and nucleophile combination as new reagent for aliphatic C–H functionalization at indole 2α-position. Org. Biomol. Chem. 11:3, pages 496-502.
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Daniel Gironés, Marcel Hanckmann, Floris P. J. T. Rutjes & Floris L. van Delft. (2012) 2′-Modified Neamine Analogues from Thiomannosides through Glycosidation-Stereoinversion. European Journal of Organic Chemistry 2012:25, pages 4740-4750.
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Kosuke Kakita, Toshifumi Tsuda, Noritoshi Suzuki, Seiichi Nakamura, Hisanori Nambu & Shunichi Hashimoto. (2012) A stereocontrolled construction of 2-azido-2-deoxy-1,2-cis-α-galactosidic linkages utilizing 2-azido-4,6-O-benzylidene-2-deoxygalactopyranosyl diphenyl phosphates: stereoselective synthesis of mucin core 5 and core 7 structures. Tetrahedron 68:25, pages 5005-5017.
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Martin A. Fascione, Sophie J. Adshead, Pintu K. Mandal, Colin A. Kilner, Andrew G. Leach & W. Bruce Turnbull. (2012) Mechanistic Studies on a Sulfoxide Transfer Reaction Mediated by Diphenyl Sulfoxide/Triflic Anhydride. Chemistry – A European Journal 18:10, pages 2987-2997.
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Ryan M. Schmaltz, Sarah R. Hanson & Chi-Huey Wong. (2011) Enzymes in the Synthesis of Glycoconjugates. Chemical Reviews 111:7, pages 4259-4307.
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Tongzhong Ju, Vivianne I. Otto & Richard D. Cummings. (2011) The Tn Antigen—Structural Simplicity and Biological Complexity. Angewandte Chemie International Edition 50:8, pages 1770-1791.
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Tongzhong Ju, Vivianne I. Otto & Richard D. Cummings. (2011) Das Tn‐Antigen – strukturell einfach und biologisch komplex. Angewandte Chemie 123:8, pages 1808-1830.
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David J. Harvey. (2010) Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for the period 2005–2006. Mass Spectrometry Reviews 30:1, pages 1-100.
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Olaf R. Ludek, Wenlu Gu & Jeffrey C. Gildersleeve. (2010) Activation of glycosyl trichloroacetimidates with perchloric acid on silica (HClO4–SiO2) provides enhanced α-selectivity. Carbohydrate Research 345:14, pages 2074-2078.
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Therese Buskas, Pamela Thompson & Geert‐Jan Boons. 2009. Carbohydrate‐Based Vaccines and Immunotherapies. Carbohydrate‐Based Vaccines and Immunotherapies 263 311 .

Sampat Ingale, Margreet A. Wolfert, Therese Buskas & Geert-Jan Boons. (2009) Increasing the Antigenicity of Synthetic Tumor-Associated Carbohydrate Antigens by Targeting Toll-Like Receptors. ChemBioChem 10:3, pages 455-463.
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David P. Gamblin, Eoin M. Scanlan & Benjamin G. Davis. (2008) Glycoprotein Synthesis: An Update. Chemical Reviews 109:1, pages 131-163.
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Robert V. Stick & Spencer J. Williams. 2009. Carbohydrates: The Essential Molecules of Life. Carbohydrates: The Essential Molecules of Life 203 223 .

Yusuf Vohra, Mahalakshmi Vasan, Andre Venot & Geert-Jan Boons. (2008) One-Pot Synthesis of Oligosaccharides by Combining Reductive Openings of Benzylidene Acetals and Glycosylations. Organic Letters 10:15, pages 3247-3250.
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Jana Rauvolfova, Andre Venot & Geert-Jan Boons. (2008) Chemo-enzymatic synthesis of C-9 acetylated sialosides. Carbohydrate Research 343:10-11, pages 1605-1611.
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Adeline Miermont, Hannah Barnhill, Erica Strable, Xiaowei Lu, Katherine A. Wall, Qian Wang, M. G. Finn & Xuefei Huang. (2008) Cowpea Mosaic Virus Capsid: A Promising Carrier for the Development of Carbohydrate Based Antitumor Vaccines. Chemistry – A European Journal 14:16, pages 4939-4947.
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Sampat Ingale, Margreet A Wolfert, Jidnyasa Gaekwad, Therese Buskas & Geert-Jan Boons. (2007) Robust immune responses elicited by a fully synthetic three-component vaccine. Nature Chemical Biology 3:10, pages 663-667.
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Sampat Ingale, Therese Buskas & Geert-Jan Boons. (2006) Synthesis of Glyco(lipo)peptides by Liposome-Mediated Native Chemical Ligation. Organic Letters 8:25, pages 5785-5788.
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Therese Buskas, Sampat Ingale & Geert-Jan Boons. (2006) Glycopeptides as versatile tools for glycobiology. Glycobiology 16:8, pages 113R-136R.
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David Cato, Therese Buskas & Geert‐Jan Boons. (2005) Highly Efficient Stereospecific Preparation of Tn and TF Building Blocks Using Thioglycosyl Donors and the Ph 2 SO/Tf 2 O Promoter System. . ChemInform 36:52.
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Highly Efficient Stereospecific Preparation of Tn and TF Building Blocks Using Thioglycosyl Donors and the Ph₂SO/Tf₂O Promotor SystemFootnote*
* Dedicated to the memory of Professor Jacques H. van Boom

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Highly Efficient Stereospecific Preparation of Tn and TF Building Blocks Using Thioglycosyl Donors and the Ph2SO/Tf2O Promotor SystemFootnote** Dedicated to the memory of Professor Jacques H. van Boom

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Highly Efficient Stereospecific Preparation of Tn and TF Building Blocks Using Thioglycosyl Donors and the Ph₂SO/Tf₂O Promotor SystemFootnote*
* Dedicated to the memory of Professor Jacques H. van Boom