Literature DB >> 15010751

Chemoselective ligation in glycochemistry.

Francesco Peri1, Francesco Nicotra.   

Abstract

This feature article describes chemoselective techniques for the assembly of neoglycopeptides and oligosaccharide mimics. Chemoselective ligation, allowing the use of aqueous environments and non-protected substrates, provides rapid access to complex glycoconjugates. The role of these molecules in recognition, signal transduction pathways and other events of fundamental biomedical significance is an object of study in the emerging field of chemical glycomics.

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Year:  2003        PMID: 15010751     DOI: 10.1039/b308907j

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  13 in total

1.  Assessment of chemoselective neoglycosylation methods using chlorambucil as a model.

Authors:  Randal D Goff; Jon S Thorson
Journal:  J Med Chem       Date:  2010-10-25       Impact factor: 7.446

2.  Enhancement of cyclopamine via conjugation with nonmetabolic sugars.

Authors:  Randal D Goff; Jon S Thorson
Journal:  Org Lett       Date:  2012-04-27       Impact factor: 6.005

3.  Sigmatropic rearrangements as tools for amino acid and peptide modification: application of the allylic sulfur ylide rearrangement to the preparation of neoglycoconjugates and other conjugates.

Authors:  David Crich; Yekui Zou; Franck Brebion
Journal:  J Org Chem       Date:  2006-11-24       Impact factor: 4.354

4.  Glycosyloxyamine neoglycosylation: a model study using calicheamicin.

Authors:  Randal D Goff; Shanteri Singh; Jon S Thorson
Journal:  ChemMedChem       Date:  2011-02-23       Impact factor: 3.466

Review 5.  Clustered carbohydrates in synthetic vaccines.

Authors:  Francesco Peri
Journal:  Chem Soc Rev       Date:  2012-12-18       Impact factor: 54.564

6.  Neo-glycopeptides: the importance of sugar core conformation in oxime-linked glycoprobes for interaction studies.

Authors:  Carmen Jiménez-Castells; Beatriz G de la Torre; David Andreu; Ricardo Gutiérrez-Gallego
Journal:  Glycoconj J       Date:  2008-08-01       Impact factor: 2.916

7.  Allylic selenosulfide rearrangement: a method for chemical ligation to cysteine and other thiols.

Authors:  David Crich; Venkataramanan Krishnamurthy; Thomas K Hutton
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419

8.  Enhancing the divergent activities of betulinic acid via neoglycosylation.

Authors:  Randal D Goff; Jon S Thorson
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

9.  Dechalcogenative allylic selenosulfide and disulfide rearrangements: complementary methods for the formation of allylic sulfides in the absence of electrophiles. Scope, limitations, and application to the functionalization of unprotected peptides in aqueous media.

Authors:  David Crich; Venkataramanan Krishnamurthy; Franck Brebion; Maheswaran Karatholuvhu; Venkataraman Subramanian; Thomas K Hutton
Journal:  J Am Chem Soc       Date:  2007-07-27       Impact factor: 15.419

10.  Synthesis of neoglycoconjugates by the desulfurative rearrangement of allylic disulfides.

Authors:  David Crich; Fan Yang
Journal:  J Org Chem       Date:  2008-08-27       Impact factor: 4.354

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