Literature DB >> 21815670

The total synthesis of immunostimulant α-galactosylceramides from naturally configured α-galactoside raffinose.

Zhenxing Zhang1, Wei Zhao, Bin Wang, Chengfeng Xia, Wenpeng Zhang, Peng George Wang.   

Abstract

The total synthesis of absolute anomeric confirmation α-galactosylceramide analogues from raffinose is described. Using the naturally occurring α-galactoside raffinose as the starting material, the easily maneuverable protocol without glycosylation reactions ensured the critical α-linkage in the product and simplified the synthetic procedures. The immunostimulatory activities of the new α-galactosylceramides were validated by both in vitro and in vivo NKT cell stimulation assays.

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Year:  2011        PMID： 21815670      PMCID： PMC3398385          DOI： 10.1021/ol201695n

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


  28 in total

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Authors:  Tetsuya Toba; Kenji Murata; Kyoko Nakanishi; Bitoku Takahashi; Naohiro Takemoto; Minako Akabane; Takashi Nakatsuka; Seiichi Imajo; Takashi Yamamura; Sachiko Miyake; Hirokazu Annoura
Journal:  Bioorg Med Chem Lett       Date:  2007-03-03       Impact factor: 2.823

2.  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

3.  Extended applications of di-tert-butylsilylene-directed alpha-predominant galactosylation compatible with C2-participating groups toward the assembly of various glycosides.

Authors:  Akihiro Imamura; Akiyoshi Kimura; Hiromune Ando; Hideharu Ishida; Makoto Kiso
Journal:  Chemistry       Date:  2006-11-24       Impact factor: 5.236

4.  Efficient synthesis of alpha-galactosyl ceramide analogues using glycosyl iodide donors.

Authors:  Wenjun Du; Jacquelyn Gervay-Hague
Journal:  Org Lett       Date:  2005-05-12       Impact factor: 6.005

5.  Differential recognition of CD1d-alpha-galactosyl ceramide by the V beta 8.2 and V beta 7 semi-invariant NKT T cell receptors.

Authors:  Daniel G Pellicci; Onisha Patel; Lars Kjer-Nielsen; Siew Siew Pang; Lucy C Sullivan; Konstantinos Kyparissoudis; Andrew G Brooks; Hugh H Reid; Stephanie Gras; Isabelle S Lucet; Ruide Koh; Mark J Smyth; Thierry Mallevaey; Jennifer L Matsuda; Laurent Gapin; James McCluskey; Dale I Godfrey; Jamie Rossjohn
Journal:  Immunity       Date:  2009-07-17       Impact factor: 31.745

6.  Alpha-lactosylceramide as a novel "sugar-capped" CD1d ligand for natural killer T cells: biased cytokine profile and therapeutic activities.

Authors:  Wenpeng Zhang; Xincheng Zheng; Chengfeng Xia; Ramu Sridhar Perali; Qingjia Yao; Yang Liu; Pan Zheng; Peng George Wang
Journal:  Chembiochem       Date:  2008-06-16       Impact factor: 3.164

7.  Synthesis and in vivo evaluation of 4-deoxy-4,4-difluoro-KRN7000.

Authors:  Leo Leung; Cyrille Tomassi; Katrien Van Beneden; Tine Decruy; Dirk Elewaut; Tim Elliott; Aymen Al-Shamkhani; Christian Ottensmeier; Serge Van Calenbergh; Joern Werner; Tony Williams; Bruno Linclau
Journal:  Org Lett       Date:  2008-09-18       Impact factor: 6.005

8.  De novo synthesis of a D-galacturonic acid thioglycoside as key to the total synthesis of a glycosphingolipid from Sphingomonas yanoikuyae.

Authors:  Pierre Stallforth; Alexander Adibekian; Peter H Seeberger
Journal:  Org Lett       Date:  2008-03-26       Impact factor: 6.005

9.  Glycolipid antigen drives rapid expansion and sustained cytokine production by NK T cells.

Authors:  Nadine Y Crowe; Adam P Uldrich; Konstantinos Kyparissoudis; Kirsten J L Hammond; Yoshihiro Hayakawa; Stephané Sidobre; Rachael Keating; Mitchell Kronenberg; Mark J Smyth; Dale I Godfrey
Journal:  J Immunol       Date:  2003-10-15       Impact factor: 5.422

10.  Rapid identification of immunostimulatory alpha-galactosylceramides using synthetic combinatorial libraries.

Authors:  Qian Li; Rachel M Ndonye; Petr A Illarionov; Karl O A Yu; Elliot S Jerud; Kristine Diaz; Gabriel Bricard; Steven A Porcelli; Gurdyal S Besra; Young-Tae Chang; Amy R Howell
Journal:  J Comb Chem       Date:  2007-09-27
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  1 in total

1.  Thermodynamic and Structural Behavior of α-Galactosylceramide and C6-Functionalized α-GalCer in 2D Layers at the Air-Liquid Interface.

Authors:  Gerald Brezesinski; Adam D J Calow; Claney L Pereira; Peter H Seeberger
Journal:  Chembiochem       Date:  2019-11-07       Impact factor: 3.164
  1 in total

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