Literature DB >> 15876055

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

Wenjun Du1, Jacquelyn Gervay-Hague.   

Abstract

The combination of reactive galactosyl iodide donors with electron-rich acceptor lipids provides highly stereoselective and efficient routes to alpha GalCer analogues. Using per-O-silylated donors, key intermediates can be obtained in a three-step, one-pot sequence providing useful constructs for analogue development.

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Year:  2005        PMID： 15876055     DOI： 10.1021/ol050659f

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


  22 in total

1.  Apoptosis-induced inhibition of CD1d-mediated antigen presentation: different roles for caspases and signal transduction pathways.

Authors:  Masood A Khan; Venkataraman Sriram; Gourapura J Renukaradhya; Wenjun Du; Jacquelyn Gervay-Hague; Randy R Brutkiewicz
Journal:  Immunology       Date:  2008-03-14       Impact factor: 7.397

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

Authors:  Zhenxing Zhang; Wei Zhao; Bin Wang; Chengfeng Xia; Wenpeng Zhang; Peng George Wang
Journal:  Org Lett       Date:  2011-08-04       Impact factor: 6.005

3.  One-pot syntheses of immunostimulatory glycolipids.

Authors:  Matthew Schombs; Francine E Park; Wenjun Du; Suvarn S Kulkarni; Jacquelyn Gervay-Hague
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

4.  A threonine-based targeting signal in the human CD1d cytoplasmic tail controls its functional expression.

Authors:  Jianyun Liu; Daniel Shaji; Sungyoo Cho; Wenjun Du; Jacquelyn Gervay-Hague; Randy R Brutkiewicz
Journal:  J Immunol       Date:  2010-04-05       Impact factor: 5.422

5.  Design, Synthesis, and Immunological Evaluation of Benzyloxyalkyl-Substituted 1,2,3-Triazolyl α-GalCer Analogues.

Authors:  Yogesh Kumar Verma; Bonam Srinivasa Reddy; Mithun S Pawar; Debabrata Bhunia; Halmuthur M Sampath Kumar
Journal:  ACS Med Chem Lett       Date:  2015-12-10       Impact factor: 4.345

6.  Design and Evaluation of ω-Hydroxy Fatty Acids Containing α-GalCer Analogues for CD1d-Mediated NKT Cell Activation.

Authors:  Chaemin Lim; Jae Hyun Kim; Dong Jae Baek; Joo-Youn Lee; Minjae Cho; Yoon-Sook Lee; Chang-Yuil Kang; Doo Hyun Chung; Won-Jae Cho; Sanghee Kim
Journal:  ACS Med Chem Lett       Date:  2014-02-04       Impact factor: 4.345

7.  Heteroaromatic Moieties in the Sphingosine Backbone of α-Galactosylceramides for Noncovalent Interactions with CD1d.

Authors:  Yongju Kim; Jonghoon Kim; Keunhee Oh; Dong-Sup Lee; Seung Bum Park
Journal:  ACS Med Chem Lett       Date:  2012-01-10       Impact factor: 4.345

8.  A Thr/Ser dual residue motif in the cytoplasmic tail of human CD1d is important for the down-regulation of antigen presentation following a herpes simplex virus 1 infection.

Authors:  Jianyun Liu; Nicole L Glosson; Wenjun Du; Jacquelyn Gervay-Hague; Randy R Brutkiewicz
Journal:  Immunology       Date:  2013-10       Impact factor: 7.397

9.  Two-step synthesis of the immunogenic bacterial glycolipid BbGL1.

Authors:  Suvarn S Kulkarni; Jacquelyn Gervay-Hague
Journal:  Org Lett       Date:  2008-09-18       Impact factor: 6.005

10.  Design and efficient synthesis of novel GM2 analogues with respect to the elucidation of the function of GM2 activator.

Authors:  Tatsuya Komori; Takayuki Ando; Akihiro Imamura; Yu-Teh Li; Hideharu Ishida; Makoto Kiso
Journal:  Glycoconj J       Date:  2008-03-27       Impact factor: 2.916
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