Literature DB >> 21384825

A fluorous phosphate protecting group with applications to carbohydrate synthesis.

Lin Liu1, Nicola L B Pohl.   

Abstract

The first fluorous protecting group for phosphate is reported. This group can be used as a facile tag for purification and be removed under mild reducing conditions using zinc and ammonium formate. Synthesis of a disaccharide from Leishmania using this fluorous protecting group demonstrated the group's stability to the acidic conditions necessary for glycosylation as well as its orthogonality to several other common protecting groups.

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Year:  2011        PMID： 21384825      PMCID： PMC3127408          DOI： 10.1021/ol2003435

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  22 in total

1.  Introduction of 2,2,2-trichloroethyl-protected sulfates into monosaccharides with a sulfuryl imidazolium salt and application to the synthesis of sulfated carbohydrates.

Authors:  Laura J Ingram; Scott D Taylor
Journal:  Angew Chem Int Ed Engl       Date:  2006-05-19       Impact factor: 15.336

2.  The total synthesis of moenomycin A.

Authors:  James G Taylor; Xuechen Li; Markus Oberthür; Wenjiang Zhu; Daniel E Kahne
Journal:  J Am Chem Soc       Date:  2006-11-29       Impact factor: 15.419

3.  Synthesis, biological activity, and molecular modeling studies of 1H-1,2,3-triazole derivatives of carbohydrates as alpha-glucosidases inhibitors.

Authors:  Sabrina B Ferreira; Ana C R Sodero; Mariana F C Cardoso; Emerson S Lima; Carlos R Kaiser; Floriano P Silva; Vitor F Ferreira
Journal:  J Med Chem       Date:  2010-03-25       Impact factor: 7.446

Review 4.  How phosphotransferase system-related protein phosphorylation regulates carbohydrate metabolism in bacteria.

Authors:  Josef Deutscher; Christof Francke; Pieter W Postma
Journal:  Microbiol Mol Biol Rev       Date:  2006-12       Impact factor: 11.056

5.  Toward solution-phase automated iterative synthesis: fluorous-tag assisted solution-phase synthesis of linear and branched mannose oligomers.

Authors:  Firoz A Jaipuri; Nicola L Pohl
Journal:  Org Biomol Chem       Date:  2008-05-16       Impact factor: 3.876

6.  Fluorous-based carbohydrate microarrays.

Authors:  Kwang-Seuk Ko; Firoz A Jaipuri; Nicola L Pohl
Journal:  J Am Chem Soc       Date:  2005-09-28       Impact factor: 15.419

7.  Fluorous Boc ((F)Boc) carbamates: new amine protecting groups for use in fluorous synthesis.

Authors:  Z Luo; J Williams; R W Read; D P Curran
Journal:  J Org Chem       Date:  2001-06-15       Impact factor: 4.354

8.  Fluorous affinity purification of oligonucleotides.

Authors:  William H Pearson; David A Berry; Patrick Stoy; Kee-Yong Jung; Anthony D Sercel
Journal:  J Org Chem       Date:  2005-09-02       Impact factor: 4.354

9.  Mono- Vs. Di-flourous tagged Glucosamines for Iterative Oligosaccharide Synthesis.

Authors:  Gisun Park; Kwang-Seuk Ko; Aleksandra Zakharova; Nicola L Pohl
Journal:  J Fluor Chem       Date:  2008-10       Impact factor: 2.050

10.  Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative.

Authors:  Masazumi Iwashita; Kumiko Makide; Taro Nonomura; Yoshimasa Misumi; Yuko Otani; Mayuko Ishida; Ryo Taguchi; Masafumi Tsujimoto; Junken Aoki; Hiroyuki Arai; Tomohiko Ohwada
Journal:  J Med Chem       Date:  2009-10-08       Impact factor: 7.446
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  10 in total

1.  Recent progress on fluorous synthesis of biologically interesting compounds.

Authors:  Zhong-Xing Jiang; Sanjun Zhi; Wei Zhang
Journal:  Mol Divers       Date:  2014-01-20       Impact factor: 2.943

2.  Automated fluorous-assisted solution-phase synthesis of β-1,2-, 1,3-, and 1,6-mannan oligomers.

Authors:  Shu-Lun Tang; Nicola L B Pohl
Journal:  Carbohydr Res       Date:  2016-04-06       Impact factor: 2.104

3.  Novel Organophosphate Ligand O-(2-Fluoroethyl)-O-(p-Nitrophenyl)Methylphosphonate: Synthesis, Hydrolytic Stability and Analysis of the Inhibition and Reactivation of Cholinesterases.

Authors:  Chih-Kai Chao; S Kaleem Ahmed; John M Gerdes; Charles M Thompson
Journal:  Chem Res Toxicol       Date:  2016-10-17       Impact factor: 3.739

4.  Regioselective Benzylation of 2-Deoxy-2-Aminosugars Using Crown Ethers: Application to a Shortened Synthesis of Hyaluronic Acid Oligomers.

Authors:  Chinmoy Mukherjee; Lin Liu; Nicola L B Pohl
Journal:  Adv Synth Catal       Date:  2014-07-07       Impact factor: 5.837

5.  HPLC-Assisted Automated Oligosaccharide Synthesis: Implementation of the Autosampler as a Mode of the Reagent Delivery.

Authors:  Salvatore G Pistorio; Swati S Nigudkar; Keith J Stine; Alexei V Demchenko
Journal:  J Org Chem       Date:  2016-09-14       Impact factor: 4.354

6.  Assembly of a Complex Branched Oligosaccharide by Combining Fluorous-Supported Synthesis and Stereoselective Glycosylations using Anomeric Sulfonium Ions.

Authors:  Wei Huang; Qi Gao; Geert-Jan Boons
Journal:  Chemistry       Date:  2015-08-06       Impact factor: 5.236

7.  Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry.

Authors:  Swati S Nigudkar; Alexei V Demchenko
Journal:  Chem Sci       Date:  2015-05-01       Impact factor: 9.825

8.  Recyclable fluorous-tag assisted two-directional oligosaccharide synthesis enabled by interrupted Pummerer reaction mediated glycosylation.

Authors:  Lei Cai; Qi Chen; Jian Guo; Zhihua Liang; Dengxian Fu; Lingkui Meng; Jing Zeng; Qian Wan
Journal:  Chem Sci       Date:  2022-06-22       Impact factor: 9.969

9.  Automated Solution-Phase Synthesis of β-1,4-Mannuronate and β-1,4-Mannan.

Authors:  Shu-Lun Tang; Nicola L B Pohl
Journal:  Org Lett       Date:  2015-05-08       Impact factor: 6.005

Review 10.  Leloir Glycosyltransferases in Applied Biocatalysis: A Multidisciplinary Approach.

Authors:  Luuk Mestrom; Marta Przypis; Daria Kowalczykiewicz; André Pollender; Antje Kumpf; Stefan R Marsden; Isabel Bento; Andrzej B Jarzębski; Katarzyna Szymańska; Arkadiusz Chruściel; Dirk Tischler; Rob Schoevaart; Ulf Hanefeld; Peter-Leon Hagedoorn
Journal:  Int J Mol Sci       Date:  2019-10-23       Impact factor: 5.923
  10 in total

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