136743-49-2Relevant academic research and scientific papers
A short, versatile chemical synthesis of L- And D-amino acids stereoselectively labelled solely in the beta position
Lowpetch, Kreingkrai,Young, Douglas W.
, p. 3348 - 3356 (2007/10/03)
L- and D-Amino acids which are stereoselectively labelled solely either in the 3-pro-R or in the 3-pro-S-positions have been prepared by a relatively short chemical synthesis in ee of 81 to 86%. This involves Sharpless' aminohydroxylation and cyclisation
Versatile Synthesis of Stereospecifically Labelled D-Amino Acids via Labelled Aziridines - Preparation of (2R,3S)-- and (2R,3R)--Serine; (2S,2'S,3S,3'S)-- and (2S,2'S,3R,3'R)--Cystine; and (2S,3S)- and (2S,3R)--β-Chloroalanine
Axelsson, B. Svante,O'Toole, Kevin J.,Spencer, Philip A.,Young, Douglas W.
, p. 807 - 816 (2007/10/02)
Stereospecifically β-labelled protected 2-carboxyaziridines 2, with the stereochemistry of a D-amino acid at C-2, have been prepared by a chemicoenzymic synthesis.Preparation of the labelled malates 5, by hydration of fumaric acid using the enzyme fumarase or by amination with aspartase followed by nitrosation, was followed by conversion into the isoserines 3, by a process involving Curtius rearrangement with retention of stereochemistry at the chirally labelled primary centre.Protection and ring closure gave the aziridines 2, which, on ring opening with the appropriate nucleophiles and deprotection, gave stereospecifically labelled samples of D-serine 16, D-cystine 20 and β-chloro-D-alanine 22.
A Versatile Synthesis of Stereospecifically Labelled D-Amino Acids and Related Enzyme inhibitors
Axelsson, B. Svante,O'Toole, Kevin J.,Spencer, Philip A.,Young, Douglas W.
, p. 1085 - 1086 (2007/10/02)
Stereospecifically deuteriated isoserines 4, formed from enzymically prepared 3-deuteriated malic acids 2 (X=OH) by Curtius rearrangement, have been converted to the deuteriated aziridines 7 and 9 which, on ring-opening and deprotection, yielded samples o
