Literature DB >> 22042483

Divergent synthetic approach to 6''-modified α-GalCer analogues.

Nora Pauwels1, Sandrine Aspeslagh, Gerd Vanhoenacker, Koen Sandra, Esther D Yu, Dirk M Zajonc, Dirk Elewaut, Bruno Linclau, Serge Van Calenbergh.   

Abstract

A synthetic approach is presented for the synthesis of galacturonic acid and D-fucosyl modified KRN7000. The approach allows for late-stage functionalisation of both the sugar 6''-OH and the sphingosine amino groups, which enables convenient synthesis of promising 6''-modified KRN7000 analogues.

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Year:  2011        PMID： 22042483      PMCID： PMC3246390          DOI： 10.1039/c1ob06235b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  39 in total

1.  Total synthesis of alpha-galactosyl cerebroside.

Authors:  S Figueroa-Pérez; R R Schmidt
Journal:  Carbohydr Res       Date:  2000-09-08       Impact factor: 2.104

2.  Glycolipid antigen processing for presentation by CD1d molecules.

Authors:  T I Prigozy; O Naidenko; P Qasba; D Elewaut; L Brossay; A Khurana; T Natori; Y Koezuka; A Kulkarni; M Kronenberg
Journal:  Science       Date:  2001-01-26       Impact factor: 47.728

3.  A phase I study of the natural killer T-cell ligand alpha-galactosylceramide (KRN7000) in patients with solid tumors.

Authors:  Giuseppe Giaccone; Cornelis J A Punt; Yoshitaka Ando; Rita Ruijter; Nobusuke Nishi; Marlies Peters; B Mary E von Blomberg; Rik J Scheper; Hans J J van der Vliet; Alfons J M van den Eertwegh; Marja Roelvink; Jos Beijnen; Heinz Zwierzina; Herbert M Pinedo
Journal:  Clin Cancer Res       Date:  2002-12       Impact factor: 12.531

4.  Synthesis and NKT cell stimulating properties of fluorophore- and biotin-appended 6"-amino-6"-deoxy-galactosylceramides.

Authors:  Xiao-Ti Zhou; Claire Forestier; Randal D Goff; Chunhong Li; Luc Teyton; Albert Bendelac; Paul B Savage
Journal:  Org Lett       Date:  2002-04-18       Impact factor: 6.005

5.  Effects of lipid chain lengths in alpha-galactosylceramides on cytokine release by natural killer T cells.

Authors:  Randal D Goff; Ying Gao; Jochen Mattner; Dapeng Zhou; Ning Yin; Carlos Cantu; Luc Teyton; Albert Bendelac; Paul B Savage
Journal:  J Am Chem Soc       Date:  2004-10-27       Impact factor: 15.419

Review 6.  The stimulating adventure of KRN 7000.

Authors:  Aline Banchet-Cadeddu; Eric Hénon; Manuel Dauchez; Jean-Hugues Renault; Fanny Monneaux; Arnaud Haudrechy
Journal:  Org Biomol Chem       Date:  2011-03-11       Impact factor: 3.876

7.  Synthesis of alpha-galactosyl ceramide, a potent immunostimulatory agent.

Authors:  Oliver Plettenburg; Vera Bodmer-Narkevitch; Chi-Huey Wong
Journal:  J Org Chem       Date:  2002-06-28       Impact factor: 4.354

8.  Immunostimulatory and antitumor activities of monoglycosylceramides having various sugar moieties.

Authors:  K Motoki; M Morita; E Kobayashi; T Uchida; K Akimoto; H Fukushima; Y Koezuka
Journal:  Biol Pharm Bull       Date:  1995-11       Impact factor: 2.233

9.  Structure-activity relationship of alpha-galactosylceramides against B16-bearing mice.

Authors:  M Morita; K Motoki; K Akimoto; T Natori; T Sakai; E Sawa; K Yamaji; Y Koezuka; E Kobayashi; H Fukushima
Journal:  J Med Chem       Date:  1995-06-09       Impact factor: 7.446

10.  Synthesis of a versatile building block for the preparation of 6-N-derivatized α-galactosyl ceramides: rapid access to biologically active glycolipids.

Authors:  Peter J Jervis; Liam R Cox; Gurdyal S Besra
Journal:  J Org Chem       Date:  2010-12-14       Impact factor: 4.354
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  9 in total

1.  Synthesis of C-5″ and C-6″-modified α-GalCer analogues as iNKT-cell agonists.

Authors:  Joren Guillaume; Nora Pauwels; Sandrine Aspeslagh; Dirk M Zajonc; Dirk Elewaut; Serge Van Calenbergh
Journal:  Bioorg Med Chem       Date:  2015-05-04       Impact factor: 3.641

2.  4"-O-Alkylated α-Galactosylceramide Analogues as iNKT-Cell Antigens: Synthetic, Biological, and Structural Studies.

Authors:  Jonas Janssens; Aruna Bitra; Jing Wang; Tine Decruy; Koen Venken; Johan van der Eycken; Dirk Elewaut; Dirk M Zajonc; Serge van Calenbergh
Journal:  ChemMedChem       Date:  2018-12-17       Impact factor: 3.466

3.  Amide-Linked C4″-Saccharide Modification of KRN7000 Provides Potent Stimulation of Human Invariant NKT Cells and Anti-Tumor Immunity in a Humanized Mouse Model.

Authors:  Noemi Alejandra Saavedra-Avila; Santosh Keshipeddy; Matthew J Guberman-Pfeffer; Ayax Pérez-Gallegos; Neeraj K Saini; Carolina Schäfer; Leandro J Carreño; José A Gascón; Steven A Porcelli; Amy R Howell
Journal:  ACS Chem Biol       Date:  2020-12-09       Impact factor: 5.100

4.  Enhanced TCR footprint by a novel glycolipid increases NKT-dependent tumor protection.

Authors:  Sandrine Aspeslagh; Marek Nemčovič; Nora Pauwels; Koen Venken; Jing Wang; Serge Van Calenbergh; Dirk M Zajonc; Dirk Elewaut
Journal:  J Immunol       Date:  2013-08-19       Impact factor: 5.422

5.  Synthesis and Anti-Influenza A Virus Activity of 6'-amino-6'-deoxy-glucoglycerolipids Analogs.

Authors:  Li Ren; Jun Zhang; Haizhen Ma; Linlin Sun; Xiaoshuang Zhang; Guangli Yu; Huashi Guan; Wei Wang; Chunxia Li
Journal:  Mar Drugs       Date:  2016-06-18       Impact factor: 5.118

6.  Efficient Divergent Synthesis of New Immunostimulant 4″-Modified α-Galactosylceramide Analogues.

Authors:  Jonas Janssens; Tine Decruy; Koen Venken; Toshiyuki Seki; Simon Krols; Johan Van der Eycken; Moriya Tsuji; Dirk Elewaut; Serge Van Calenbergh
Journal:  ACS Med Chem Lett       Date:  2017-05-05       Impact factor: 4.345

Review 7.  Tailored design of NKT-stimulatory glycolipids for polarization of immune responses.

Authors:  Jung-Tung Hung; Jing-Rong Huang; Alice L Yu
Journal:  J Biomed Sci       Date:  2017-03-23       Impact factor: 8.410

Review 8.  Antigen specificity of invariant natural killer T-cells.

Authors:  Alysia M Birkholz; Mitchell Kronenberg
Journal:  Biomed J       Date:  2016-03-10       Impact factor: 4.910

9.  Natural Killer T Cell-Targeted Immunotherapy Mediating Long-term Memory Responses and Strong Antitumor Activity.

Authors:  Nyambayar Dashtsoodol; Tomokuni Shigeura; Takuya Tashiro; Minako Aihara; Toshihiro Chikanishi; Hiromi Okada; Keigo Hanada; Hirokazu Sano; Akihiko Kurogi; Masaru Taniguchi
Journal:  Front Immunol       Date:  2017-09-25       Impact factor: 7.561
  9 in total

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