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Chemoselective ligation refers to the use of mutually specific reactive chemical groups to accomplish molecular conjugation. Staudinger chemistry, based on the. Research Article. Traceless Staudinger Ligation for Biotinylation of Acetylated Thiol-Azido Heterobifunctional Linker and Its Attachment to Gold Surface. Bioconjugation techniques using organic azides are compared in this critical review. A particular focus is on chemical ligation reactions and.


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Rapid Staudinger Ligation on Cell Surfaces :: ChemViews Magazine :: ChemistryViews

Therefore the strength of the binding did not reveal severe competition from the phenyl groups of the spacers. In addition to closed configurations of 4 and 6 in water formed by intramolecular staudinger ligation inclusion, open configurations are additionally present, which promote intermolecular aggregation and staudinger ligation account for the slow Brownian motion of the dimer in the aqueous solution.


The fact that in DMSO staudinger ligation linkers prefer to reside over the cavity indicates that intermediate conformations, between extended and self-included may exist in water as well. Computational results Quantum mechanical calculations were carried out for monomer 4 and dimer 6 at the PM3 level of theory for isolated molecules, as well as in staudinger ligation presence of solvent water at the PM3 COSMO level of theory in order to assess solvation effects.


The calculated geometries were sorted out into three limiting configurations: Thus, semiempirical as well as DFT calculations suggest that both compounds prefer to adopt conformations with the phenyl groups either staudinger ligation the CD cavity staudinger ligation or over the C6 area vicinal of comparable energies, therefore they may easily interconvert.

Typical conformations of 6: Staudinger ligation an all-gg conformation of C5-C6OH in 4, phenyl inclusion via the primary side was more thermochemically favored by ca.

Finally, in the open structures the shortest distances observed were with the cavity exterior H1, H2 and H4.

Staudinger ligation as a method for bioconjugation.

The accommodation of the protonated form of 1-adamantylmine inside the cavity of monomer 4 was also explored at the PM3 COSMO level of theory.

A variety of initial complex geometries was considered consisting of vicinal as well as of inclusion configurations for 4. Its accommodation into the inclusion configuration proceeds by a push of staudinger ligation phenyl ring.

A new double Staudinger linker has been specifically developed to allow homodimer formation in one step. Despite the well verified formation of intra- as well as staudinger ligation inclusion complexes, the compounds proved to be effective in encapsulating a suitable external guest in each cavity.

Traceless Staudinger Ligation for Studying Ubiquitin-Mediated Protein Degradation - Langdon Martin

Angew Chem Int Ed Engl. For example, the Staudinger ligation has been utilized to label glycans, lipids, DNA, and proteins. Moreover, the Staudinger ligation has been used as a synthetic method to construct glycopeptides, microarrays, and functional biopolymers.

Epub Staudinger ligation 2.

Staudinger ligation as a method for bioconjugation. A traceless version of the reaction leaves behind no residual atoms.