Assymetric synthesis of (2S,3R)- and (2S,3S)-[2-13C;3-2H] glutamic acid

SAIL – stereo-array isotope labeling

“…However, (2S,3S)-and (2S,3R)-[2-13 C;3-2 H]glutamic acid can be obtained from commercially available materials by a straightforward synthesis via the asymmetric hydrogenation of a 2,3-didehydroamino acid derivative using an a-oxoglutarate or a dehydroserine derivative as the starting material (Okuma et al 2009). This report describes a simple method for the synthesis of [2-13 C;3-2 H] glutamic acid, routed through ornithine as the key intermediate.…”

“…Although several groups had reported the stereoselective synthesis of glutamic acid derivatives with stereospecific deuterium labeling, these synthetic routes were not suitable for regioselective 13 C labeling coupled with deuterium labeling because the starting 13 C-labeled materials were unavailable. However, (2 S ,3 S )- and (2 S ,3 R )-[2- 13 C;3- 2 H]glutamic acid can be obtained from commercially available materials by a straightforward synthesis via the asymmetric hydrogenation of a 2,3-didehydroamino acid derivative using an α-oxoglutarate or a dehydroserine derivative as the starting material (Okuma et al 2009). This report describes a simple method for the synthesis of [2- 13 C;3- 2 H] glutamic acid, routed through ornithine as the key intermediate.…”

1.12 Labeling Techniques

“…This has been achieved by chemical and enzymatic reactions using starting materials uniformly labeled with 13 C and 15 N. [35][36][37][38][39][40] As previously mentioned, the SAIL amino acids are commercially Figure 2 Chemical structures of 20 SAIL amino acids. This has been achieved by chemical and enzymatic reactions using starting materials uniformly labeled with 13 C and 15 N. [35][36][37][38][39][40] As previously mentioned, the SAIL amino acids are commercially Figure 2 Chemical structures of 20 SAIL amino acids.…”

Isotope Labelling

“…In the case of the aromatic groups of Phe, Tyr and Trp, the absence of one-bond carbon-carbon coupling eliminates the need for a constant time scheme, thereby reducing the duration of the pulse scheme [141,142]. To perform this method, 20 special amino acids with a complete stereo-and regio-specific pattern of isotope labelling (SAIL amino acids) have been chemically and enzymatically synthesised (Figure 2.2) [25,[142][143][144]. These SAIL amino acids are commercially available from SAILTechnologies, a company that was established to supply SAIL amino acids to the NMR community (www.sail-technologies.com).…”