392232-75-6Relevant academic research and scientific papers
A novel synthesis of N-methyl asparagine, arginine, histidine, and tryptophan
Aurelio, Luigi,Brownlee, Robert T. C.,Hughes, Andrew B.
, p. 3767 - 3769 (2002)
(graph presented) R = CH2(3-indolyl) tryptophan R = CH2CONH2 asparagine R = CH2(2-imidazolyl) histidine R = CH2CH2CH2(guanidyl) arginine N-Methyl amino acid residues in peptides
An efficient synthesis of N-methyl amino acids by way of intermediate 5-oxazolidinones
Aurelio, Luigi,Box, John S.,Brownlee, Robert T. C.,Hughes, Andrew B.,Sleebs, Marianne M.
, p. 2652 - 2667 (2007/10/03)
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.
