TY - JOUR
T1 - A new route to "bifunctional" chelating agents
T2 - Conversion of amino acids to analogs of ethylenedinitrilotetraacetic acid
AU - Yeh, Simon M.
AU - Sherman, David G.
AU - Meares, Claude F.
PY - 1979/11/15
Y1 - 1979/11/15
N2 - Via the amides, α-amino acids can be converted to analogs of ethylenedinitrilotetraacetic acid, with retention of configuration at the asymmetric carbon. 1-(p-Carboxymethoxybenzyl)-ethylenedinitrilotetraacetic acid has been prepared from l-tyrosine and then coupled as the iron(III) chelate to 1,2-diaminoethane or to human serum albumin. The iron(III) chelate is effective in preventing EDTA carboxyl groups from reacting via carbodiimide coupling with amino groups. After the coupling reaction, iron is readily removed from the chelate upon reduction with ascorbate. These new procedures possess several attractive features for the use of "bifunctional" chelating agents in biophysical studies.
AB - Via the amides, α-amino acids can be converted to analogs of ethylenedinitrilotetraacetic acid, with retention of configuration at the asymmetric carbon. 1-(p-Carboxymethoxybenzyl)-ethylenedinitrilotetraacetic acid has been prepared from l-tyrosine and then coupled as the iron(III) chelate to 1,2-diaminoethane or to human serum albumin. The iron(III) chelate is effective in preventing EDTA carboxyl groups from reacting via carbodiimide coupling with amino groups. After the coupling reaction, iron is readily removed from the chelate upon reduction with ascorbate. These new procedures possess several attractive features for the use of "bifunctional" chelating agents in biophysical studies.
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U2 - 10.1016/0003-2697(79)90125-8
DO - 10.1016/0003-2697(79)90125-8
M3 - Article
C2 - 120685
AN - SCOPUS:0018593125
VL - 100
SP - 152
EP - 159
JO - Analytical Biochemistry
JF - Analytical Biochemistry
SN - 0003-2697
IS - 1
ER -