108732-30-5Relevant academic research and scientific papers
A NEW SYNTHETIC EQUIVALENT OF THE GLUTAMIC ACID γ-ANION AND ITS APPLICATION TO THE SYNTHESIS OF S-(+)-γ-CARBOXYGLUTAMIC ACID
Attwood, Michael R.,Carr, Maria G.,Jordan, Steven
, p. 283 - 284 (1990)
Protected S-pyroglutamic acid can be deprotonated specifically at the γ-position.The resulting enolate can be converted into γ-carboxyglutamic acid in optically pure form.
The synthesis and properties of Gla- and Phe-containing analogues of cyclic RGD pentapeptides
Davies, John S.,Enjalbal, Christine,Nguyen, Corrine,Al-Jamri, Loai,Naumer, Christian
, p. 2907 - 2915 (2007/10/03)
Cyclopentapeptides containing the Arg-Gly-Asp motif have been synthesised using solid-phase assembly of side-chain-protected linear precursors, followed by solution-phase cyclisation. The replacement of the Asp residue by γ-carboxyglutamic acid (Gla) is a novel feature which gives rise to an analogue which inhibits cell adhesion, yet its congeners do not show activity in binding assays with recombinant integrin receptors. NMR techniques support a β/γ-turn conformation in most of the analogues. The Royal Society of Chemistry 2000.
A New Approach for the Total Synthesis of L-γ-Carboxyglutamic Acid: Utility of Ruthenium Tetroxide Oxidation
Tanaka, Ken-ichi,Yoshifuji, Shigeyuki,Nitta, Yoshihiro
, p. 3879 - 3884 (2007/10/02)
A new and convenient synthesis of optically pure L-γ-carboxyglutamic acid (L-Gla)(1) from L-proline as a chiral source was developed.Protection of N-tert-butyloxycarbonyl(Boc)prolinol (4) with a tert-butyldimethylsilyl group followed by oxidation with ruthenium tetroxide (RuO4) afforded the corresponding lactam compound (6), which was carboxylated with lithium diisopropylamide and benzyloxycarbonylimidazole to afford the 4-benzyloxycarbonyl lactam derivative (7).Selective removal of the silyl group from 7, followed by oxidation of the resulting alcohol (8) with pyridinium dichromate gave the carboxylic acid, which was converted into the ester derivatives (10b-d).Cleavage of the lactam bond of 10b with excess benzyl alcohol in the presence of triethylamine gave γ,γ,α-tribenzyl N-Boc-L-γ-carboxyglutamate (11).Finally, 11 was hydrogenated over Pd on charcoal and deprotected with trifluoroacetic acid to produce L-γ-carboxyglutamic acid (1).Keywords - L-γ-carboxyglutamic acid; ruthenium tetroxide oxidation; carboxylation; L-proline; L-prolinol; 1-benzyloxycarbonylimidazole; 4-benzyloxycarbonyl-1-tert-butyloxycarbonyl-L-pyroglutamic acid ester; catalytic hydrogenation; trifluoroacetic acid deprotection
