Premium
Trimetaphosphate‐Induced Addition of Aspartic Acid to Oligo(glutamic acid)s
Author(s) -
Hill Aubrey,
Orgel Leslie E.
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200290009
Subject(s) - chemistry , aspartic acid , glutamic acid , glycine , amine gas treating , histidine , amino acid , organic chemistry , stereochemistry , medicinal chemistry , biochemistry
When a solution containing 0.01 M decaglutamic acid, 0.1–1.0 M aspartic acid, 1.0 M MgCl 2 , and 0.5 M sodium trimetaphosphate is allowed to stand at temperatures in the range 0–50°, addition products containing up to ten aspartic acid residues are formed. Addition occurs to the side‐chain carboxy moieties, not to the terminal amine of the decaglutamic acid. A number of other amino acids including glutamic acid, glycine, and histidine fail to react with decaglutamic acid under the same conditions. We believe that the activation of aspartic acid leads to the formation of a cyclic anhydride that is the key intermediate in the reaction.