D-Biotinyl-OSu contains a biotin moiety linked through an O-succinimidyl (OSu) ester, classifying it as a biotinylated N-hydroxysuccinimide ester amino-acid-derived labeling reagent rather than a free amino acid. The molecule bears an activated ester functional group that can undergo nucleophilic acyl substitution with primary amines to form stable amide bonds, while the biotin scaffold provides a distinct affinity handle for capture-based workflows. D-Biotinyl-OSu is used in chemical biology and analytical chemistry for preparing biotinylated proteins, peptides, or other amine-containing targets, as well as for generating biotin-tagged conjugates for affinity purification and downstream detection.
CAT No: CP27040
CAS No:35013-72-0
Synonyms/Alias:35013-72-0;(+)-BiotinN-hydroxysuccinimideester;Biotin-NHS;2,5-Dioxopyrrolidin-1-yl5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate;N-SuccinimidylD-biotinate;BNHS;d-BiotinNHSester;N-Hydroxysuccinimidobiotin;Biotinyl-N-hydroxy-succinimide;(+)-BiotinN-succinimidylester;MFCD00078531;BiotinN-HydroxysuccinimideEster;D-Biotinyl-osu;Biotin-NHester;Biotin-OSu;BHSE;(+)-Biotin-NHS;biotinsuccinimidylester;AC1O8JYD;biotin-N-hydroxysuccinimide;SCHEMBL81912;KBioGR_002486;KBioSS_002493;N-(D-Biotinyloxy)succinimide;H1759_SIGMA
D-Biotinyl-OSu is a biotin-based activated ester (N-hydroxysuccinimide ester) designed for amide bond formation with primary amines under mild, aqueous-compatible conditions. The structure couples a chiral biotin scaffold to an OSu leaving group, providing a stable electrophile at the carbonyl while preserving the ureido ring and valeric acid side chain that support strong avidin/streptavidin recognition. The activated ester functionality reacts with lysine residues, amino-containing linkers, and amine-functional polymers, enabling controlled bioconjugation while minimizing side reactions associated with more reactive acyl chlorides. Stereochemical considerations are primarily governed by the biotin framework, and the resulting biotinylated amide products maintain the stereochemically defined binding epitope for downstream affinity capture and analytical detection.
1. Bioconjugation Chemistry
D-Biotinyl-OSu is used in chemical biology and bioconjugation workflows to attach biotin to proteins, peptides, and amine-bearing biomolecules through NHS ester acylation. The OSu-activated carbonyl targets nucleophilic primary amines, while the biotin moiety provides a high-affinity handle for avidin/streptavidin-based enrichment, blotting, and pull-down assays. The amide linkage formed downstream yields a stable conjugate suitable for subsequent labeling steps, affinity purification, and assay development. Biotinylated targets prepared from D-Biotinyl-OSu can serve as standardized reagents for studying binding interactions, immobilizing biomolecules on solid supports, and generating affinity-tagged constructs for research and applied diagnostics.
2. Protein Engineering
D-Biotinyl-OSu supports protein engineering efforts that require site-selective or controlled biotin tagging of lysine-rich proteins and engineered variants containing accessible amine groups. The reagent's NHS ester group enables coupling to protein surface amines, and the resulting biotinylated amide maintains the biotin binding face needed for avidin-mediated immobilization. The biotin handle can be used to construct protein arrays, enable immobilized enzyme assays, and facilitate structural studies where controlled surface attachment is required. Downstream, biotinylated proteins can be employed as affinity-capture reagents in workflow automation, including purification steps and analytical readouts that rely on biotin-streptavidin interactions.
3. Analytical Research Standards
D-Biotinyl-OSu is applied in analytical chemistry to prepare biotinylated standards, calibration reagents, and internal controls for affinity-based detection methods. The activated ester chemistry enables incorporation of biotin into amine-containing analytes, peptides, or polymeric matrices that can then be captured on streptavidin-coated surfaces for signal generation. The stable amide bond improves conjugate robustness during washing and sample handling, supporting reproducible assay performance in method development and validation contexts. Biotinylated reference materials derived from D-Biotinyl-OSu can also be used for LC-MS/MS method development, immunoassay optimization, and surface chemistry screening where consistent biotin density and linkage stability matter.
4. Solid-Phase Immobilization
D-Biotinyl-OSu is suitable for constructing immobilized biomolecule platforms used in screening, biosensing, and affinity purification technologies. The NHS ester reacts with amine-functional resins, beads, and surfaces, while the biotin moiety provides a secondary binding layer for streptavidin capture or direct biotin recognition depending on the immobilization strategy. The resulting biotinylated linkages can improve orientation control of biomolecules on solid phases and enable modular assembly of multi-component systems such as enzyme cascades and binding assays. Industrially, this chemistry can translate into manufacturing-relevant workflows for generating affinity capture media, reusable reagent supports, and consistent solid-phase formats for applied research and chemical manufacturing operations.
5. Polymer And Surface Modification
D-Biotinyl-OSu enables polymer modification and interface functionalization where incorporation of biotin into amine-bearing polymers, coatings, or biomaterial surfaces is required. The OSu activated ester participates in acylation of primary amines on polymer backbones or pendant groups, forming stable amide linkages that retain the biotin recognition epitope. The biotin-functional polymers can then be used for affinity-driven assembly, controlled immobilization of enzymes or antibodies, and surface patterning strategies that rely on streptavidin bridging. Downstream, biotinylated polymer conjugates can function as intermediates for specialty chemical production, including formulation components for immobilized biocatalysis systems and functional material platforms requiring robust affinity handles.
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