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Saponification of esters of chiral α‐amino acids anchored through their amine function on solid support
Author(s) -
Cantel Sonia,
Desgranges Stéphane,
Martinez Jean,
Fehrentz JeanAlain
Publication year - 2004
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.561
Subject(s) - saponification , racemization , chemistry , amine gas treating , amino acid , residue (chemistry) , organic chemistry , solid phase synthesis , cleavage (geology) , carboxylic acid , high performance liquid chromatography , chromatography , peptide , biochemistry , fracture (geology) , geotechnical engineering , engineering
Anchoring an α‐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 α‐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. Copyright © 2004 European Peptide Society and John Wiley & Sons, Ltd.