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For protein conjugations, the linker needs to have various functional groups (e.g., disulfide, maleimide, halogen acetamide) to allow the reaction with cysteines from biomolecules. NHS ester, isocyanate, and isothiocyanate can also be used for labeling lysines. Another example of bioconjugation involves bioorthogonal reactions where a biomolecule with ketone or aldehyde is conjugated with hydroxylamines or hydrazides functionalized linkers.
Additional examples in the context of protein conjugations include ligations (see ligation technologies) or site-selective labeling (e.g., with a propargyl tag). For oligonucleotides, bioconjugation can be performed with cholesterol, fatty acids, or GalNAc using corresponding phosphoramidites. In chemical biology, ligation technologies encompass a diverse set of methods used to covalently join two or more biomolecules, such as peptides, proteins, nucleic acids, or carbohydrates.
These techniques are pivotal for studying and manipulating biological systems, enabling the creation of novel biomolecular constructs, probes, and therapeutics. Several key ligation technologies commonly employed in chemical biology include copper-catalyzed azide-alkyne cycloaddition (CuAAC), strain-promoted azide-alkyne cycloaddition (SPAAC), and disulfide bond formation.
Bioconjugates are formed by covalently linking biologically active molecules, such as small molecules, peptides, and proteins, to other chemical entities. This capability allows us to create bespoke bioconjugates that serve as powerful tools for probing biological systems, imaging, and therapeutic applications.
Our expertise includes site-specific conjugation, scalable synthesis, and thorough analytical characterization, ensuring that each bioconjugate meets the highest standards of quality and performance. We offer custom synthesis of fluorescent probes, homo- and hetero-bifunctional molecules, and other specialized bioconjugates.
Leveraging innovative techniques and state-of-the-art equipment, we provide innovative solutions that address the most challenging aspects of chemical biology research. Our bioconjugation techniques enable the precise attachment of biomolecules to various substrates, facilitating the study of complex biological processes and the development of targeted therapies.
Many different approaches to the synthesis of long peptides or protein constructs via ligation of unprotected peptides have been performed at SpiroChem: beyond the formation of triazoles from azides and alkynes, we also use hydrazone ligation between aldehydes or ketones and oxime formation from hydroxylamines and aldehydes or ketones.
SpiroChem also has experience in dipeptide formation via 4-component reaction (amine, acid, isonitrile, aziridine aldehyde) and imine ligation between amine and aldehyde. Other examples include thiazolidine ligation from cysteine and α-ester aldehyde, peptide bond formation from native chemical ligation (CNL) from thio- or seleno esters and amines, traceless Staudinger ligation from azides and thioesters modified with trialkyl phosphines, and α-ketoacid–hydroxylamine (KAHA) ligation.
SpiroChem has the expertise and equipment to tackle problems in any of these or related fields. Our experienced team works closely with clients to tailor each project to their specific needs, ensuring optimal results and advancing the field of chemical biology. Furthermore, SpiroChem can leverage its state-of-the-art analytical chemistry platform to support chemical biology projects.
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