Carboxylate-Directed Pd-Catalyzed β-C(sp3)–H Arylation of N-Methyl Alanine Derivatives for Diversification of Bioactive Peptides
- 12 December 2023
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 25 (50) , 9008-9013
Abstract
This study presents a Pd(II)-catalyzed method for the β-C(sp3)-H arylation of N-Cbz- or N-Fmoc-protected N-methyl alanines, providing ready access to building blocks for N-methylated peptide synthesis. For this transformation, the native carboxylate was exploited as the directing group, attributing its success to the use of a monoprotected amino-pyridine ligand. Its synthetic utility was demonstrated by facile generation of nine analogues of the naturally occurring N-methylated cyclic peptide cycloaspeptide A.Keywords
Funding Information
- National Research Foundation of Korea (NRF-2021R1A4A1032114, NRF-2022R1C1C1004049, NRF-2021R1A2C1094331)
- Korea Basic Science Institute (2019R1A6C1010028)
This publication has 62 references indexed in Scilit:
- Nonnatural Amino Acid Synthesis by Using Carbon–Hydrogen Bond Functionalization MethodologyAngewandte Chemie International Edition, 2012
- On the SelectiveN-Methylation of BOC-Protected Amino AcidsThe Journal of Organic Chemistry, 2009
- Cycloaspeptides F and G, Cyclic Pentapeptides from a Cordyceps-Colonizing Isolate of Isaria farinosaJournal of Natural Products, 2009
- Palladium(II)‐Catalyzed C-H Activation/C-C Cross‐Coupling Reactions: Versatility and PracticalityAngewandte Chemie International Edition, 2009
- Copper(I) Coordination Chemistry of (Pyridylmethyl)amide LigandsInorganic Chemistry, 2006
- Convenient Synthesis ofN-Methylamino Acids Compatible with Fmoc Solid-Phase Peptide SynthesisThe Journal of Organic Chemistry, 2005
- Synthetic Preparation of N-Methyl-α-amino AcidsChemical Reviews, 2004
- Site-Selective N-Methylation of Peptides on Solid SupportJournal of the American Chemical Society, 1997
- Platinum(II) catalysed selective remote oxidation of unactivated C–H bonds in aliphatic carboxylic acidsJournal of the Chemical Society, Chemical Communications, 1991
- Studies on fungal products. XI Isolation and structures of novel cyclic pentapeptides from Aspergillus sp. NE-45.Chemical and Pharmaceutical Bulletin, 1987