Literature DB >> 19802334

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

Gisun Park1, Kwang-Seuk Ko, Aleksandra Zakharova, Nicola L Pohl.   

Abstract

Fluorous-tagged protecting groups are attractive tools for elongating carbohydrate chains in oligosaccharide synthesis. To eliminate the accumulation of failed sequences during automated oligosaccharide synthesis conditions, an additional C(8)F(17) ester derived protecting group was attached to the glycosyl donor to better retain the desired doubly-tagged glycosylation product on fluorous solid phase extraction (FSPE) cartridges. Initial studies show that the double-fluorous-tagging strategy offers a robust enough separation using a commercial FSPE cartridge using simple gravity filtration to separate the desired product from the singly-fluorous-tagged starting materials and their decomposition products. In addition, removal of the fluorous acetate and its byproducts after sodium methoxide treatment and neutralization required only dissolution of the desired sugar in toluene and subsequent removal of the toluene layer from the denser fluorous byproducts.

Entities:  

Year:  2008        PMID： 19802334      PMCID： PMC2613283          DOI： 10.1016/j.jfluchem.2008.05.001

Source DB:  PubMed          Journal:  J Fluor Chem        ISSN： 0022-1139            Impact factor:   2.050


  26 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

2.  Solution-phase mixture synthesis with double-separation tagging: double demixing of a single mixture provides a stereoisomer library of 16 individual murisolins.

Authors:  Craig S Wilcox; Venugopal Gudipati; Hejun Lu; Serhan Turkyilmaz; Dennis P Curran
Journal:  Angew Chem Int Ed Engl       Date:  2005-10-28       Impact factor: 15.336

3.  Solid-phase oligosaccharide tagging (SPOT): Validation on glycolipid-derived structures.

Authors:  Anders Lohse; Rita Martins; Malene Ryborg Jørgensen; Ole Hindsgaul
Journal:  Angew Chem Int Ed Engl       Date:  2006-06-19       Impact factor: 15.336

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.  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.  "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

Review 8.  Synthesis and medical applications of oligosaccharides.

Authors:  Peter H Seeberger; Daniel B Werz
Journal:  Nature       Date:  2007-04-26       Impact factor: 49.962

Review 9.  Cycling of O-linked beta-N-acetylglucosamine on nucleocytoplasmic proteins.

Authors:  Gerald W Hart; Michael P Housley; Chad Slawson
Journal:  Nature       Date:  2007-04-26       Impact factor: 49.962

10.  Solution-phase mixture synthesis with fluorous tagging en route: total synthesis of an eight-member stereoisomer library of passifloricins.

Authors:  Dennis P Curran; Gustavo Moura-Letts; Matthias Pohlman
Journal:  Angew Chem Int Ed Engl       Date:  2006-04-03       Impact factor: 15.336
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  5 in total

1.  Fluorous-Assisted One-Pot Oligosaccharide Synthesis.

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

2.  A fluorous phosphate protecting group with applications to carbohydrate synthesis.

Authors:  Lin Liu; Nicola L B Pohl
Journal:  Org Lett       Date:  2011-03-08       Impact factor: 6.005

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

Authors:  Fa Zhang; Wei Zhang; Yan Zhang; Dennis P Curran; Gang Liu
Journal:  J Org Chem       Date:  2009-03-20       Impact factor: 4.354

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

Authors:  Yan Zhang; Bo Liu; Gang Liu
Journal:  Mol Divers       Date:  2013-05-22       Impact factor: 2.943

5.  Synthesis of fluorous photolabile aldehyde and carbamate and alkyl carbamate protecting groups for carbohydrate-associated amines.

Authors:  Rajarshi Roychoudhury; Nicola L B Pohl
Journal:  Org Lett       Date:  2014-02-10       Impact factor: 6.005
  5 in total

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