Saponification of esters of chiral alpha-amino acids anchored through their amine function on solid support.
Anchoring an alpha-amino acid residue by its amine function onto a solid support is an alternative to develop chemistry on its carboxylic function. This strategy can involve the use of amino-acid esters as precursors of the carboxylic function. A complete study on the Wang-resin was performed to determine the non racemizing saponification conditions of anchored alpha-amino esters. The use of LiOH, NaOH, NaOSi(Me)3, various solvents and temperatures were tested for this reaction. After saponification and cleavage from the support, samples were examined through their Marfey's derivatives by reversed phase HPLC to evaluate the percentage of racemization.
Cantel
Sonia
S
Laboratoire des Aminoacides, Peptides et Protéines, UMR 5810 CNRS Université Montpellier I et II, Faculté de Pharmacie, 15 Avenue Charles Flahault, BP 14491, 34093 Montpellier Cédex 5, France.
Desgranges
Stéphane
S
Martinez
Jean
J
Fehrentz
Jean-Alain
JA
D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D006868:Hydrolysis; D015394:Molecular Structure; D013237:Stereoisomerism
D000588:Amines; D000596:Amino Acids; D004952:Esters