Literature DB >> 20518525

Synthesis of immunostimulatory alpha-C-galactosylceramide glycolipids via Sonogashira coupling, asymmetric epoxidation, and trichloroacetimidate-mediated epoxide opening.

Zheng Liu1, Hoe-Sup Byun, Robert Bittman.   

Abstract

Stereocontrolled syntheses of alpha-C-GalCer (2) and its alpha-C-acetylenic analogue 6 were accomplished in high efficiency by a convergent construction strategy from 1-hexadecene and d-galactose. The key transformations include Sonogashira coupling, Sharpless asymmetric epoxidation, and Et(2)AlCl-catalyzed cyclization of an epoxytrichloroacetimidate to generate protected dihydrooxazine 21.

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Year:  2010        PMID： 20518525      PMCID： PMC2896489          DOI： 10.1021/ol1009976

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


  26 in total

1.  The crystal structure of human CD1d with and without alpha-galactosylceramide.

Authors:  Michael Koch; Victoria S Stronge; Dawn Shepherd; Stephan D Gadola; Bini Mathew; Gerd Ritter; Alan R Fersht; Gurdyal S Besra; Richard R Schmidt; E Yvonne Jones; Vincenzo Cerundolo
Journal:  Nat Immunol       Date:  2005-07-10       Impact factor: 25.606

2.  Expedient synthesis of the alpha-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000).

Authors:  Peter Wipf; Joshua G Pierce
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

3.  Structural evaluation of potent NKT cell agonists: implications for design of novel stimulatory ligands.

Authors:  André Schiefner; Masakazu Fujio; Douglass Wu; Chi-Huey Wong; Ian A Wilson
Journal:  J Mol Biol       Date:  2009-09-02       Impact factor: 5.469

4.  A stereocontrolled, efficient synthetic route to bioactive sphingolipids: synthesis of phytosphingosine and phytoceramides from unsaturated ester precursors via cyclic sulfate intermediates.

Authors:  L He; H S Byun; R Bittman
Journal:  J Org Chem       Date:  2000-11-03       Impact factor: 4.354

5.  Efficient synthesis of alpha-C-galactosyl ceramide immunostimulants: use of ethylene-promoted olefin cross-metathesis.

Authors:  Guangwu Chen; John Schmieg; Moriya Tsuji; Richard W Franck
Journal:  Org Lett       Date:  2004-10-28       Impact factor: 6.005

6.  A synthetic glycolipid prevents autoimmune encephalomyelitis by inducing TH2 bias of natural killer T cells.

Authors:  K Miyamoto; S Miyake; T Yamamura
Journal:  Nature       Date:  2001-10-04       Impact factor: 49.962

7.  Reactions of alkenylchromium reagents prepared from alkenyl trifluoromethanesulfonates (triflates) with chromium(II) chloride under nickel catalysis.

Authors:  K Takai; M Tagashira; T Kuroda; K Oshima; K Utimoto; H Nozaki
Journal:  J Am Chem Soc       Date:  1986-09-01       Impact factor: 15.419

8.  Invariant TCR rather than CD1d shapes the preferential activities of C-glycoside analogues against human versus murine invariant NKT cells.

Authors:  Xiangming Li; Takayuki Shiratsuchi; Guangwu Chen; Paolo Dellabona; Giulia Casorati; Richard W Franck; Moriya Tsuji
Journal:  J Immunol       Date:  2009-09-04       Impact factor: 5.422

9.  C-Galactosylceramide Diastereomers via Sharpless Asymmetric Epoxidation Chemistry.

Authors:  Jun Pu; Richard W Franck
Journal:  Tetrahedron       Date:  2008-09-08       Impact factor: 2.457

10.  A multifactorial mechanism in the superior antimalarial activity of alpha-C-GalCer.

Authors:  John Schmieg; Guangli Yang; Richard W Franck; Moriya Tsuji
Journal:  J Biomed Biotechnol       Date:  2009-12-27
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  12 in total

1.  C-Galactosylceramide: Synthesis and Immunology.

Authors:  Richard W Franck
Journal:  C R Chim       Date:  2012-01-01       Impact factor: 3.117

2.  Total synthesis of α-1C-galactosylceramide, an immunostimulatory C-glycosphingolipid, and confirmation of the stereochemistry in the first-generation synthesis.

Authors:  Zheng Liu; Hoe-Sup Byun; Robert Bittman
Journal:  J Org Chem       Date:  2011-10-04       Impact factor: 4.354

Review 3.  Raising the roof: the preferential pharmacological stimulation of Th1 and th2 responses mediated by NKT cells.

Authors:  James E East; Andrew J Kennedy; Tonya J Webb
Journal:  Med Res Rev       Date:  2012-12-13       Impact factor: 12.944

4.  Synthesis and biological activities of C-glycosides of KRN 7000 with novel ceramide residues.

Authors:  Ahmad S Altiti; Xiaojing Ma; Lixing Zhang; Yi Ban; Richard W Franck; David R Mootoo
Journal:  Carbohydr Res       Date:  2017-03-06       Impact factor: 2.104

5.  NKT TCR recognition of CD1d-α-C-galactosylceramide.

Authors:  Onisha Patel; Garth Cameron; Daniel G Pellicci; Zheng Liu; Hoe-Sup Byun; Travis Beddoe; James McCluskey; Richard W Franck; A Raúl Castaño; Youssef Harrak; Amadeu Llebaria; Robert Bittman; Steven A Porcelli; Dale I Godfrey; Jamie Rossjohn
Journal:  J Immunol       Date:  2011-09-30       Impact factor: 5.422

6.  Synthesis of C-glycoside analogues of α-galactosylceramide via linear allylic C-H oxidation and allyl cyanate to isocyanate rearrangement.

Authors:  Zheng Liu; Robert Bittman
Journal:  Org Lett       Date:  2012-01-10       Impact factor: 6.005

7.  C-Glycosphingolipids with an exo-methylene substituent: stereocontrolled synthesis and immunostimulation of mouse and human natural killer T lymphocytes.

Authors:  Zheng Liu; Amy N Courtney; Leonid S Metelitsa; Robert Bittman
Journal:  Chembiochem       Date:  2012-07-10       Impact factor: 3.164

8.  C-glycosphingolipid precursors via iodocyclization of homoallyic trichloroacetimidates.

Authors:  Ahmad S Altiti; David R Mootoo
Journal:  Carbohydr Res       Date:  2015-02-21       Impact factor: 2.104

9.  The Crotylation Way to Glycosphingolipids: Synthesis of Analogues of KRN7000.

Authors:  Ahmad S Altiti; Stewart Bachan; David R Mootoo
Journal:  Org Lett       Date:  2016-08-25       Impact factor: 6.005

10.  Intramolecular nitrogen delivery for the synthesis of C-glycosphingolipids. Application to the C-glycoside of the immunostimulant KRN7000.

Authors:  Ahmad S Altiti; David R Mootoo
Journal:  Org Lett       Date:  2014-02-21       Impact factor: 6.005
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