Phenylboronic acid complexing reagents derived from aminosalicyl

Details Phenylboronic acid complexing reagents derived from aminosalicyl Phenylboronic acid complexing reagents derived from aminosalicyl

1994-01-28

1997-01-14

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546291, 546292, 54620564/, 5462074/, 546158, 546213, 546214, 546220, 546246, 558 8, 558 17, 560315, 562 26, 562453, 562622, 562624, C07C25910

Patent

active

055941516

ABSTRACT:
The present invention relates to a novel class of phenylboronic acid complexing reagents useful for the preparation of bioconjugates, and the method of making and using such reagents. In the present invention, in the place of prior art Avidin-Biotin and Digoxigenin-anti-Digoxigenin systems, phenylboronic acid complexing reagents are utilized in conjunction with phenylboronic acid reagents (many of which are known in the prior art) to facilitate chemical conjugation without the use of intermediary biological macromolecules. Reagents suitable for the modification of a bioactive species for the purpose of incorporating a phenylboronic acid complexing moiety for subsequent conjugation to a different bioactive species having pendant phenylboronic acid moleties are of General Formula I or General Formula II. ##STR1## wherein group X is selected from either H, OH, NH.sub.2, NHCH.sub.3, NHOH and NHOCH.sub.3, wherein group Y is selected from either O, S and NH, and wherein group Z comprises a spacer which either separates the boronic acid complexing moiety from group R, as in General Formula I, or seperates two boronic acid complexing moieties, as in General Formula II. Group R is a reactive electrophilic or nucleophilic moiety suitable for reaction of the phenylboronic acid complexing reagent with a bioactive species.

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