311343-83-6Relevant articles and documents
Bifunctional boronic compound complexing reagents and complexes
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, (2008/06/13)
Reagents suitable for the modification of a bioactive species for the purpose of incorporating a bifunctional boronic compound complexing moiety for subsequent conjugation to a different (or the same) bioactive species having pendant phenylboronic acid moieties of General Formula 1, wherein group R is an electrophilic or nucleophilic moiety suitable for reaction of the putative bifunctional boronic compound complexing reagent with a bioactive species, wherein group R2 is selected from one of H and OH moieties, and wherein group R3 is selected from one of an alkyl and a methylene bearing an electronegative substituent. Group Z is a spacer selected from (CH2)n and CH2O(CH2CH2O)n2, wherein n is an integer of from 1 to 5, and wherein n2 is an integer of from 1 to 4. Each of group Z2 and Z3 is a spacer selected from CH2Ar, CH2CONHCH2Ar, CH2CONH(CH2)n3CO-NHCH2Ar, and (CH2)n4NHCO(CH2)n5CONHCH2Ar, wherein the group Ar represents the aromatic ring in the reagent of General Formula I to which the spacer Z2 or Z3 is appended, wherein n3 is an integer of from 1 to 5, wherein n4 is an integer selected from one of 2 and 3, and wherein n5 is an integer of from 1 to 4. Reaction of a reagent of General Formula I with a bioactive species affords a conjugate having pendant putative bifunctional boronic compound complexing moieties. (one or more) The conjugate may be further reacted with hydroxylamine (NH2OH) by amidation of the benzoic acid ester moiety to afford a class of bifunctional boronic compound complexing conjugate, e.g., conjugate with one or more pendant bifunctional boronic compound complexing moieties.