87770-01-2Relevant academic research and scientific papers
Reaction of γ-carboxyglutamic acid with aldehydes
Capasso, Renato,Randazzo, Giacomino,Pecci, Laura
, p. 2657 - 2664 (2007/10/02)
The DL-γ-carboxyglutamic acid (Gla) reacts quantitatively with formaldehyde to give 4,4-dicarboxyproline and with other aldehydes to give the racemic diastereoisomers of the 5-substituted 4,4-dicarboxyprolines.The pH-dependent reaction rate and the stereochemical behaviour suggest an intramolecular Manich mechanism. After heating at 100 deg C for 30 min, the 4,4-dicarboxyproline and the 5-substituted 4,4-dicarboxyprolines lose a carboxyl group from C4 to give the racemic diastereoisomers of the cyclic analogs of glutamic acid.
