acylbiotin

Acylbiotin is a class of biotin derivatives in which an acyl group is covalently attached to the biotin molecule. Depending on the site and nature of attachment, acylbiotin compounds may be described as N-acyl biotins (attached to the biotin’s nitrogen) or O-acyl biotins (esterified at the carboxyl-containing portion). The term can also refer to activated acyl derivatives of biotin used as reagents to transfer acyl groups in bioconjugation experiments.

Chemistry and preparation of acylbiotin derivatives typically involve standard acylation chemistry. Biotin can be reacted with an acid chloride or an anhydride to form the desired N- or O-acyl derivative, or coupled via carbodiimide or other activating reagents with a chosen carboxylic acid. The exact regioselectivity, stability, and reactivity depend on the reagents used and the reaction conditions. In some contexts, activated biotin esters or mixed anhydrides are employed to facilitate acyl transfer in subsequent steps.

Applications of acylbiotin derivatives include bioconjugation and affinity tagging, where the acylated biotin can serve as a reactive intermediate or a linker in the synthesis of labeled biomolecules. They are also used as intermediates in the preparation of biotin-based probes, enzymes, and affinity reagents, and in studies of acylation chemistry. Stability varies with the type of acyl group and the leaving group; many activated esters require careful handling and storage to minimize hydrolysis.

See also: biotin, acylation, NHS esters, bioconjugation.