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Literature DB >> 20832778

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

Nianhuan Yao¹, Gabriel Fung, Hamed Malekan, Long Ye, Mark J Kurth, Kit S Lam.

Abstract

The synthesis of glycosylated Fmoc amino acids by reaction of mono- and disaccharide peracetates with Fmoc amino acids having free carboxyl groups was rapidly promoted by Lewis acids (SnCl(4), BF(3)·Et(2)O) under microwave irradiation. The products are useful building blocks for the synthesis of glycopeptides.

Entities: Chemical Disease Species

Mesh：

Substances：

Year: 2010 PMID： 20832778 PMCID： PMC3207739 DOI： 10.1016/j.carres.2010.07.040

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

12 in total

1. From Glycals to Glycopeptides: A Convergent and Stereoselective Total Synthesis of a High Mannose N-Linked Glycopeptide This work was supported by the National Institutes of Health (Grant Numbers AI16943/CA28824). We thank Dr. George Sukenick of the MSKCC NMR Core Facility for NMR and mass spectral analyses (NIH Grant Number: CA08748).

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-10-16 Impact factor: 15.336

2. Synthesis of glycopeptides containing carbohydrate and Peptide recognition motifs.

Authors: H Herzner; T Reipen; M Schultz; H Kunz
Journal: Chem Rev Date: 2000-12-13 Impact factor: 60.622

Review 3. The emerging significance of O-GlcNAc in cellular regulation.

Authors: Natasha E Zachara; Gerald W Hart
Journal: Chem Rev Date: 2002-02 Impact factor: 60.622

Review 4. Protein N-glycosylation along the secretory pathway: relationship to organelle topography and function, protein quality control, and cell interactions.

Authors: Jürgen Roth
Journal: Chem Rev Date: 2002-02 Impact factor: 60.622

Review 5. Cell surface biology mediated by low affinity multivalent protein-glycan interactions.

Authors: Brian E Collins; James C Paulson
Journal: Curr Opin Chem Biol Date: 2004-12 Impact factor: 8.822

Review 6. Chemical glycobiology.

Authors: C R Bertozzi; L L Kiessling
Journal: Science Date: 2001-03-23 Impact factor: 47.728

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

2. Synthesis of glycopeptides containing carbohydrate and Peptide recognition motifs.

Review 3. The emerging significance of O-GlcNAc in cellular regulation.

Review 4. Protein N-glycosylation along the secretory pathway: relationship to organelle topography and function, protein quality control, and cell interactions.

Review 5. Cell surface biology mediated by low affinity multivalent protein-glycan interactions.

Review 6. Chemical glycobiology.

7. Solid-phase glycosylation of peptide templates and on-bead MAS-NMR analysis: perspectives for glycopeptide libraries.

8. Microwave-assisted glycosylation for the synthesis of glycopeptides.

9. Solid-phase synthesis of O-linked glycopeptide analogues of enkephalin.

10. Microwave-assisted Ullmann C-S bond formation: synthesis of the P38alpha MAPK clinical candidate VX-745.

Review 1. Opioid glycopeptide analgesics derived from endogenous enkephalins and endorphins.

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