Literature DB >> 15680608

Microwave-assisted glycosylation for the synthesis of glycopeptides.

Jürgen Seibel1, Lars Hillringhaus, Roxana Moraru.   

Abstract

An efficient one-step synthesis of O-linked glycosylamino acids is described. This methodology converts commercially available peracetylated mono- and disaccharides activated by cheap and environmentally safe FeCl(3) under microwave irradiation with Fmoc-Ser-OBn to the corresponding beta-glycosides in short reaction times and moderate yields.

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Year:  2005        PMID: 15680608     DOI: 10.1016/j.carres.2004.12.014

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN: 0008-6215            Impact factor:   2.104


  6 in total

Review 1.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

2.  Glycosylation of α-amino acids by sugar acetate donors with InBr3. Minimally competent Lewis acids.

Authors:  Mark R Lefever; Lajos Z Szabò; Bobbi Anglin; Michael Ferracane; Joanna Hogan; Lauren Cooney; Robin Polt
Journal:  Carbohydr Res       Date:  2012-01-28       Impact factor: 2.104

3.  Improving metabolic stability by glycosylation: bifunctional peptide derivatives that are opioid receptor agonists and neurokinin 1 receptor antagonists.

Authors:  Takashi Yamamoto; Padma Nair; Neil E Jacobsen; Josef Vagner; Vinod Kulkarni; Peg Davis; Shou-Wu Ma; Edita Navratilova; Henry I Yamamura; Todd W Vanderah; Frank Porreca; Josephine Lai; Victor J Hruby
Journal:  J Med Chem       Date:  2009-08-27       Impact factor: 7.446

4.  Facile synthesis of glycosylated Fmoc amino acid building blocks assisted by microwave irradiation.

Authors:  Nianhuan Yao; Gabriel Fung; Hamed Malekan; Long Ye; Mark J Kurth; Kit S Lam
Journal:  Carbohydr Res       Date:  2010-08-02       Impact factor: 2.104

5.  Microwave effect for glycosylation promoted by solid super acid in supercritical carbon dioxide.

Authors:  Hiroshi Hinou; Naohiro Saito; Masato Ogawa; Takahiko Maeda; Shin-Ichiro Nishimura
Journal:  Int J Mol Sci       Date:  2009-12-08       Impact factor: 6.208

6.  Can amphipathic helices influence the CNS antinociceptive activity of glycopeptides related to β-endorphin?

Authors:  Yingxue Li; Lindsay St Louis; Brian I Knapp; Dhanasekaran Muthu; Bobbi Anglin; Denise Giuvelis; Jean M Bidlack; Edward J Bilsky; Robin Polt
Journal:  J Med Chem       Date:  2014-03-07       Impact factor: 7.446

  6 in total

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