Expedient Synthesis of Triazole-Linked Glycosyl Amino Acids and Peptides
- 31 July 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (18) , 3123-3126
- https://doi.org/10.1021/ol048841o
Abstract
An expedient, high-yielding synthesis of two types of triazole-linked glycopeptides is described. These novel and stable glycopeptide mimics were prepared via Cu(I)-catalyzed [3 + 2] cycloaddition of either azide-functionalized glycosides and acetylenic amino acids or acetylenic glycosides and azide-containing amino acids.Keywords
This publication has 18 references indexed in Scilit:
- A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal AlkynesAngewandte Chemie International Edition in English, 2002
- Synthesis of α- and β-Glycosyl Asparagine Ethylene Isosteres (C-Glycosyl Asparagines) via Sugar Acetylenes and Garner Aldehyde CouplingThe Journal of Organic Chemistry, 2002
- Improved Solid-Phase Peptide Synthesis Method Utilizing α-Azide-Protected Amino AcidsOrganic Letters, 2001
- Stereoselective Syntheses of Peptide Derivatives with 2‐Acetamido‐3,4,6‐tri‐O‐acetyl‐1‐amino‐2‐deoxy‐β‐D‐glucopyranose by Four‐Component CondensationAngewandte Chemie International Edition in English, 1995
- 1,2,3-Triazole-[2,5-Bis-O-(tert-butyldimethylsilyl)-.beta.-D-ribofuranosyl]-3'-spiro-5''-(4''-amino-1'',2''-oxathiole 2'',2''-dioxide) (TSAO) Analogs: Synthesis and Anti-HIV-1 ActivityJournal of Medicinal Chemistry, 1994
- A new method of anomeric protection and activation based on the conversion of glycosyl azides into glycosyl fluoridesCarbohydrate Research, 1993
- Studies directed toward the design of orally active renin inhibitors. 1. Some factors influencing the absorption of small peptidesJournal of Medicinal Chemistry, 1993
- Preferred conformation of C-glycosides. 10. Synthesis and conformational analysis of carbon trisaccharidesThe Journal of Organic Chemistry, 1992
- Preferred conformation of C-glycosides. 1. Conformational similarity of glycosides and corresponding C-glycosidesThe Journal of Organic Chemistry, 1987
- Synthesis of Glycopeptides, Partial Structures of Biological Recognition Components [New Synthetic Methods (67)]Angewandte Chemie International Edition in English, 1987