Oxidative Amide Synthesis and N-Terminal α-Amino Group Ligation of Peptides in Aqueous Medium
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- 27 October 2006
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (46) , 14796-14797
- https://doi.org/10.1021/ja064479s
Abstract
A new method for oxidative synthesis of amides from alkynes and amines in high yields (up to 96%) using [Mn(2,6-Cl2TPP)Cl] 1 as a catalyst and Oxone/H2O2 as an oxidant in aqueous medium has been developed. This method could be used for N-terminal alpha-amino group ligation of unprotected peptides with aryl, aliphatic, and internal alkynes under mild conditions.Keywords
This publication has 36 references indexed in Scilit:
- Practical Synthesis of Amides from In Situ Generated Copper(I) Acetylides and Sulfonyl AzidesAngewandte Chemie International Edition in English, 2006
- Transition‐Metal Catalysis as a Tool for the Covalent Labeling of ProteinsAngewandte Chemie International Edition in English, 2006
- Chemoselective Amide Ligations by Decarboxylative Condensations of N‐Alkylhydroxylamines and α‐KetoacidsAngewandte Chemie International Edition in English, 2006
- Diels–Alder Ligation and Surface Immobilization of ProteinsAngewandte Chemie International Edition in English, 2005
- Metalloporphyrin-Catalyzed Diastereoselective Epoxidation of Allyl-Substituted AlkenesThe Journal of Organic Chemistry, 2005
- Alkyne Carbonylation by Radicals: Tin‐Radical‐Catalyzed Synthesis of α‐Methylene Amides from 1‐Alkynes, Carbon Monoxide, and AminesAngewandte Chemie International Edition in English, 2005
- A Cyclodextrin-Modified Ketoester for Stereoselective Epoxidation of AlkenesThe Journal of Organic Chemistry, 2003
- A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal AlkynesAngewandte Chemie International Edition in English, 2002
- Alkyne Oxidations by cis-Dioxoruthenium(VI) Complexes. A Formal [3 + 2] Cycloaddition Reaction of Alkynes with cis-[(Cn*)(CF3CO2)RuVIO2]ClO4 (Cn* = 1,4,7-Trimethyl-1,4,7-triazacyclononane)Journal of the American Chemical Society, 2000
- Methyltrioxorhenium-Catalyzed Oxidation of Secondary and Primary Amines with Hydrogen PeroxideBulletin of the Chemical Society of Japan, 1997