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l-Glutamic Acid and l-Lysine as Useful Building Blocks for the Preparation of Bifunctional DTPA-like Ligands

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Bracco spa, Milano Research Centre, via E. Folli 50, 20134 Milano, Italy
Cite this: Bioconjugate Chem. 1999, 10, 1, 137–140
Publication Date (Web):December 31, 1998
Copyright © 1999 American Chemical Society

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    Bisalkylation of suitably protected l-glutamic acid and l-lysine derivatives with tert-butyl N-(2-bromoethyl)iminodiacetate 2, followed by deprotection of the ω functional group affords N,N-bis[2-[bis[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]ethyl]-l-glutamic acid 1-(1,1-dimethylethyl) ester 4 and N2,N2-bis[2-[bis[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]ethyl]-l-lysine 1,1-dimethylethyl ester 7. Such compounds feature a carboxylic or an amino group, respectively, which are available for conjugation with a suitable partner via formation of an amide bond. The conjugates, which can be prepared in this way, contain a chelating subunit in which all five acetic residues of DTPA are available for the complexation of metal ions. Direct bisalkylation of glycine with 2 promptly gives N,N-bis[2-[bis[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]ethyl]glycine 11. The latter allows to achieve conjugates in which the central acetic group of DTPA is selectively converted into an acetamide.

     Presented in part at the 35th National Organic Chemistry Symposium, San Antonio, TX, June 1997.


     To whom correspondence should be addressed. Phone:  +39 02 21772353. Fax:  +39 02 26410678.

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