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Literature DB >> 20131837

Nucleophilic catalysis of carbohydrate oxime formation by anilines.

Mikkel B Thygesen¹, Henrik Munch, Jørgen Sauer, Emiliano Cló, Malene R Jørgensen, Ole Hindsgaul, Knud J Jensen.

Abstract

Chemoselective formation of glycoconjugates from unprotected glycans is needed to further develop chemical biology involving glycans. Carbohydrate oxime formation is often slow, and organocatalysis by anilines would be highly promising. Here, we present that carbohydrate oxime formation can be catalyzed with up to 20-fold increases in overall reaction rate at 100 mM aniline. Application of this methodology provided access to complex glycoconjugates.

Entities: Chemical

Mesh：

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Year: 2010 PMID： 20131837 DOI： 10.1021/jo902425v

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

21 in total

1. 4-aminophenylalanine as a biocompatible nucleophilic catalyst for hydrazone ligations at low temperature and neutral pH.

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2. One-pot preparation of labelled mannan-peptide conjugate, model for immune cell processing.

Authors: Pavol Farkaš; Alžbeta Čížová; Peter Bystrický; Lucia Paulovičová; Ema Paulovičová; Slavomír Bystrický
Journal: Glycoconj J Date: 2015-12-14 Impact factor: 2.916

3. 18F-Fluorodeoxyglycosylamines: Maillard reaction of 18F-fluorodeoxyglucose with biological amines.

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4. Receptor-mediated exopolysaccharide perception controls bacterial infection.

Authors: Y Kawaharada; S Kelly; M Wibroe Nielsen; C T Hjuler; K Gysel; A Muszyński; R W Carlson; M B Thygesen; N Sandal; M H Asmussen; M Vinther; S U Andersen; L Krusell; S Thirup; K J Jensen; C W Ronson; M Blaise; S Radutoiu; J Stougaard
Journal: Nature Date: 2015-07-08 Impact factor: 49.962

5. Versatile Methodology for Glycosurfaces: Direct Ligation of Nonderivatized Reducing Saccharides to Poly(pentafluorophenyl acrylate) Grafted Surfaces via Hydrazide Conjugation.

Authors: Li Chen; Deborah Leman; Caitlin R Williams; Karson Brooks; Duncan C Krause; Jason Locklin
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10. On the formation and properties of interstrand DNA-DNA cross-links forged by reaction of an abasic site with the opposing guanine residue of 5'-CAp sequences in duplex DNA.

Authors: Kevin M Johnson; Nathan E Price; Jin Wang; Mostafa I Fekry; Sanjay Dutta; Derrick R Seiner; Yinsheng Wang; Kent S Gates
Journal: J Am Chem Soc Date: 2013-01-11 Impact factor: 15.419

Nucleophilic catalysis of carbohydrate oxime formation by anilines.

1. 4-aminophenylalanine as a biocompatible nucleophilic catalyst for hydrazone ligations at low temperature and neutral pH.

2. One-pot preparation of labelled mannan-peptide conjugate, model for immune cell processing.

3. 18F-Fluorodeoxyglycosylamines: Maillard reaction of 18F-fluorodeoxyglucose with biological amines.

4. Receptor-mediated exopolysaccharide perception controls bacterial infection.

5. Versatile Methodology for Glycosurfaces: Direct Ligation of Nonderivatized Reducing Saccharides to Poly(pentafluorophenyl acrylate) Grafted Surfaces via Hydrazide Conjugation.

Review 6. Oximes and Hydrazones in Bioconjugation: Mechanism and Catalysis.

Review 7. Achieving Controlled Biomolecule-Biomaterial Conjugation.

8. Importance of ortho proton donors in catalysis of hydrazone formation.

9. Water-soluble organocatalysts for hydrazone and oxime formation.

10. On the formation and properties of interstrand DNA-DNA cross-links forged by reaction of an abasic site with the opposing guanine residue of 5'-CAp sequences in duplex DNA.