519156-34-4

Upstream product

• 50-00-0 formaldehyd 
• 22839-46-9 (2S,3R)-3-acetoxy-2-((benzyloxycarbonyl)amino)-butanoic acid 
• 17012-42-9 O-acetyl-L-threonine 

Downstream Products

• 519156-37-7 (2S,3R)-3-(acetyloxy)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)butanoic acid 
• 922705-60-0 (3R,4R)-4-(acetyloxy)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)pentanoic acid 
• 922705-75-7 (1R,2S)-4-diazo-1-methyl-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)-3-oxobutyl acetate 
• 519156-38-8 (2S,3R)-3-Acetoxy-2-(benzyloxycarbonyl-methyl-amino)-butyric acid; compound with dicyclohexyl-amine 

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.

Effective methods for the synthesis of N-methyl β-amino acids from all twenty common α-amino acids using 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones

N-Methyl β-amino acids are generally required for application in the synthesis of potentially bioactive modified peptides and other oligomers. Previous work highlighted the reductive cleavage of 1,3-oxazolidin-5-ones to synthesise N-methyl α-amino acids. Starting from α-amino acids, two approaches were used to prepare the corresponding N-methyl β-amino acids. First, α-amino acids were converted to N-methyl α-amino acids by the so-called '1,3-oxazolidin-5-one strategy', and these were then homologated by the Arndt-Eistert procedure to afford N-protected N-methyl β-amino acids derived from the 20 common α-amino acids. These compounds were prepared in yields of 23-57% (relative to N-methyl α-amino acid). In a second approach, twelve N-protected α-amino acids could be directly homologated by the Arndt-Eistert procedure, and the resulting β-amino acids were converted to the 1,3-oxazinan-6-ones in 30-45% yield. Finally, reductive cleavage afforded the desired N-methyl β-amino acids in 41-63% yield. One sterically congested β-amino acid, 3-methyl-3-aminobutanoic acid, did give a high yield (95%) of the 1,3-oxazinan-6-one (65), and subsequent reductive cleavage gave the corresponding AIBN-derived N-methyl β-amino acid 61 in 71% yield (Scheme 2). Thus, our protocols allow the ready preparation of all N-methyl β-amino acids derived from the 20 proteinogenic α-amino acids.

Decomposition of protonated threonine, its stereoisomers, and its homologues in the gas phase: Evidence for internal backside displacement

Protonated threonine and its allo diastereomer exhibit different proportions of collisionally activated dissociation (CAD) product ions. N-Methylation attenuates these differences. Water loss from protonated allo-threonine gives protonated trans-3-methyla