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Literature DB >> 23695441

Facile synthesis of tetrasaccharide aided by fluorous chemistry toward a dengue virus vaccine.

Abstract

We report the synthesis of a tetrasaccharide with side chain using a light-fluorous-tagged glycosyl donor through the double glycosylation and gradient fluorous solid-phase extraction by adding a little of DCM to improve the solubility for retention for the first time. This convergent method has high efficacy by saving much time and solvent.

Entities: Chemical Species

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Year: 2013 PMID： 23695441 DOI： 10.1007/s11030-013-9451-0

Source DB: PubMed Journal: Mol Divers ISSN： 1381-1991 Impact factor: 2.943

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References

24 in total

1. 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

Review 2. Neutralization and antibody-dependent enhancement of dengue viruses.

Authors: Scott B Halstead
Journal: Adv Virus Res Date: 2003 Impact factor: 9.937

3. Variable surface epitopes in the crystal structure of dengue virus type 3 envelope glycoprotein.

Authors: Yorgo Modis; Steven Ogata; David Clements; Stephen C Harrison
Journal: J Virol Date: 2005-01 Impact factor: 5.103

4. 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

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

Facile synthesis of tetrasaccharide aided by fluorous chemistry toward a dengue virus vaccine.

1. Oligosaccharide synthesis on a fluorous support.

Review 2. Neutralization and antibody-dependent enhancement of dengue viruses.

3. Variable surface epitopes in the crystal structure of dengue virus type 3 envelope glycoprotein.

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

5. New chemical and biological applications of fluorous technologies.

7. Oligosaccharide synthesis in microreactors.

8. Synthesis and applications of a light-fluorous glycosyl donor.

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

10. Convergent stereoselective synthesis of multiple sulfated GlcNα(1,4)GlcAβ(1,4) dodecasaccharides.