699006-14-9

Upstream product

• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 75315-63-8 N-(benzyloxycarbonyl)succinimide 

Downstream Products

• 699006-13-8 (S)-benzyl 4-((S)-1-acetoxyethyl)-5-oxo-oxazolidine-3-carboxylate 
• 519156-38-8 N-benzyloxycarbonyl-N-methyl-L-threonine-O-acetate dicyclohexylamine salt 
• 699006-19-4 (2S,3S)-3-acetoxy-2-((benzyloxycarbonyl)(methyl)amino)butanoic acid 

Relevant academic research and scientific papers

Determination of the complete absolute configuration of petriellin A

We report the full structural determination of the depsipeptide petriellin A. The absolute configuration of the amino acid residues, N-methyl isoleucine and N-methyl threonine, have been determined by a combination of HPLC and TLC comparison of synthetic Marfey's derivatives and Marfey's derivatives of the natural product hydrolysate. The configuration of the chiral centres in these two N-methylated residues was found to be the same as those of the common unmethylated l-amino acids. CSIRO 2006.

N-METHYL AMINO ACIDS

The present invention relates to a compound of formula (I) or (II), processes for preparing them, peptides including them and kits involving them.

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.