Polymerization of beta-amino acids in aqueous solution.
We have compared carbonyl diimidazole (CDI) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDAC) as activating agents for the oligomerization of negatively-charged alpha- and beta-amino acids in homogeneous aqueous solution. alpha-Amino acids can be oligomerized efficiently using CDI, but not by EDAC. beta-Amino acids can be oligomerized efficiently using EDAC, but not by CDI. Aspartic acid, an alpha- and beta-dicarboxylic acid is oligomerized efficiently by both reagents. These results are explained in terms of the mechanisms of the reactions, and their relevance to prebiotic chemistry is discussed.
Liu
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R
The Salk Institute for Biological Studies, San Diego, CA 92186-5800, USA.
Orgel
L E
LE
D000596:Amino Acids / Q000737:chemistry*; D002234:Carbodiimides / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D019143:Evolution, Molecular; D006863:Hydrogen-Ion Concentration; D007093:Imidazoles / Q000737:chemistry*; D009842:Oligopeptides / Q000138:chemical synthesis*; D011108:Polymers / Q000737:chemistry; D012996:Solutions; D013696:Temperature; D014867:Water
D000596:Amino Acids; D002234:Carbodiimides; D007093:Imidazoles; D009842:Oligopeptides; D011108:Polymers; D012996:Solutions; D014867:Water; C074139:1-ethyl-3-(3-dimethylaminoethyl)carbodiimide