Oligomerization of alpha-thioglutamic acid.
A decaglutamic acid primer is extended very slowly by alpha-thioglutamic acid. The addition of bicarbonate to the reaction mixture greatly accelerates the reaction. We believe the N-carboxyanhydride of glutamic acid is an intermediate in the accelerated reaction. When K3Fe(CN)6 and bicarbonate are both present in the reaction mixture, oligoglutamic acids up to at least the 15-mer are formed rapidly. The acylating agent is the oxidation product of thioglutamic acid, a diacyldisulfide.
Maurel
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Institut Jacques Monod, Departement Biologie Supramoleculaire et Cellulaire, Paris, France.
Orgel
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LE
D001639:Bicarbonates; D002851:Chromatography, High Pressure Liquid; D019418:Evolution, Chemical; D005292:Ferricyanides; D018698:Glutamic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D007202:Indicators and Reagents; D007700:Kinetics; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D000069497:Origin of Life
D001639:Bicarbonates; D005292:Ferricyanides; D007202:Indicators and Reagents; D009842:Oligopeptides; C418367:thioglutamic acid; D018698:Glutamic Acid; C028033:potassium ferricyanide