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Literature DB >> 19216499

Synthesis and applications of a light-fluorous glycosyl donor.

Fa Zhang¹, Wei Zhang, Yan Zhang, Dennis P Curran, Gang Liu.

Abstract

A new method using a light-fluorous glycosyl donor and an orthogonal tagging strategy to synthesize oligosaccharides and glycoconjugates has been developed. The glycosyl donor orthogonally protected with a C8F17-silyl tag and benzoyl groups was reacted with excess amounts of glycosyl acceptor. Fluorous solid-phase extraction separated the glycosylated product and unreacted glycosyl acceptor. This new protocol has high reaction efficiency and easy separation, which was demonstrated in the synthesis of an unprotected trisaccharide and an O-glycosylated serine in this paper.

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Year: 2009 PMID： 19216499 PMCID： PMC2754202 DOI： 10.1021/jo9000993

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

31 in total

1. Synthesis of complex carbohydrates and glycoconjugates: enzyme-based and programmable one-pot strategies.

Authors: K M Koeller; C H Wong
Journal: Chem Rev Date: 2000-12-13 Impact factor: 60.622

2. Oligosaccharide synthesis on a fluorous support.

Authors: Tsuyoshi Miura; Kohtaro Goto; Daisuke Hosaka; Toshiyuki Inazu
Journal: Angew Chem Int Ed Engl Date: 2003-05-09 Impact factor: 15.336

3. Synthesis and quantitative evaluation of Glycero-D-manno-heptose binding to concanavalin A by fluorous-tag assistance.

Authors: Firoz A Jaipuri; Beatrice Y M Collet; Nicola L Pohl
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

4. 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

5. New chemical and biological applications of fluorous technologies.

Authors: Wei Zhang; Chun Cai
Journal: Chem Commun (Camb) Date: 2008-10-14 Impact factor: 6.222

6. "Cap-Tag"-Novel Methods for the Rapid Purification of Oligosaccharides Prepared by Automated Solid-Phase Synthesis Financial support from the donors of the Petroleum Research Fund, administered by the ACS (ACS-PRF 34649-G1), Merck (Predoctoral Fellowship for E.R.P.), Boehringer-Ingelheim (Predoctoral Fellowship for E.R.P.), and the NIH (Biotechnology Training Grant for M.C.H.) is gratefully acknowledged. Funding for the MIT-DCIF Inova 501 was provided by the NSF (Award CHE-9808061). Funding for the MIT-DCIF Avance (DPX) 400 was provided by the NIH (Award 1S10RR13886-01). We thank Silicycle (Quebec City, Canada) for the generous gift of fluorous silica gel and isocyanate silica gel scavenger resin. We thank Dr. O. Plante for helpful discussions and help with the automated oligosaccharide synthesizer.

Authors: Emma R. Palmacci; Michael C. Hewitt; Peter H. Seeberger
Journal: Angew Chem Int Ed Engl Date: 2001-12-03 Impact factor: 15.336

7. Oligosaccharide synthesis in microreactors.

Authors: Frédéric R Carrel; Karolin Geyer; Jeroen D C Codée; Peter H Seeberger
Journal: Org Lett Date: 2007-05-10 Impact factor: 6.005

8. 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

Review 9. Biological roles of oligosaccharides: all of the theories are correct.

Authors: A Varki
Journal: Glycobiology Date: 1993-04 Impact factor: 4.313

10. Selective electrochemical glycosylation by reactivity tuning.

Authors: Robert R France; Richard G Compton; Benjamin G Davis; Antony J Fairbanks; Neil V Rees; Jay D Wadhawan
Journal: Org Biomol Chem Date: 2004-07-09 Impact factor: 3.876

14 in total

1. Fluorous supported modular synthesis of heparan sulfate oligosaccharides.

Authors: Chengli Zong; Andre Venot; Omkar Dhamale; Geert-Jan Boons
Journal: Org Lett Date: 2013-01-08 Impact factor: 6.005

2. Regenerative Glycosylation.

Authors: Yashapal Singh; Tinghua Wang; Scott A Geringer; Keith J Stine; Alexei V Demchenko
Journal: J Org Chem Date: 2017-12-22 Impact factor: 4.354

3. Fluorous-Assisted One-Pot Oligosaccharide Synthesis.

Authors: Bo Yang; Yuqing Jing; Xuefei Huang
Journal: European J Org Chem Date: 2010-01-27

4. OFox imidates as versatile glycosyl donors for chemical glycosylation.

Authors: Swati S Nigudkar; Tinghua Wang; Salvatore G Pistorio; Jagodige P Yasomanee; Keith J Stine; Alexei V Demchenko
Journal: Org Biomol Chem Date: 2017-01-04 Impact factor: 3.876

5. Investigation of the H-bond-mediated aglycone delivery reaction in application to the synthesis of β-glucosides.

Authors: Michael P Mannino; Jagodige P Yasomanee; Alexei V Demchenko
Journal: Carbohydr Res Date: 2018-09-22 Impact factor: 2.104

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