An efficient synthesis of N-methyl amino acids by way of intermediate 5-oxazolidinones.
N-Methyl amino acids occur in many natural products. Experimental strategies are presented for a unified approach to the synthesis of N-methyl derivatives through 5-oxazolidinones of the 20 common l-amino acids. The amino acids with reactive side chains that required protecting groups or devoted syntheses for side chain construction for N-methylation to proceed included serine, threonine, tyrosine, cysteine, methionine, tryptophan, asparagine, histidine, and arginine. The studies have provided improved methods for the preparation of N-methyl serine, threonine, and tyrosine. All 20 of the common l-amino acids are now available in suitable forms for solid or solution-phase peptide synthesis.
Aurelio
Luigi
L
Department of Chemistry, La Trobe University, Melbourne, Victoria 3086, Australia.
Box
John S
JS
Brownlee
Robert T C
RT
Hughes
Andrew B
AB
Sleebs
Marianne M
MM
D000596:Amino Acids / Q000138:chemical synthesis*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007202:Indicators and Reagents; D008745:Methylation; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
D000596:Amino Acids; D007202:Indicators and Reagents; D023303:Oxazolidinones