Stereoselective Synthesis of α‐ and β‐Glycofuranosyl Amides by Traceless Ligation of Glycofuranosyl Azides

Nisic, Filippo; Speciale, Gaetano; Bernardi, Anna

doi:10.1002/chem.201200309

Cited by 34 publications

(23 citation statements)

References 126 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For these reasons, the traceless variant was used for the connection and chemoselective modification of peptides and proteins . Other applications consist of the fluorescence labeling of bioactive molecules, the modification of polymers, the preparation of special lactams, or the synthesis of glycosyl amides …”

Section: Traceless Variant Of the Staudinger Ligationmentioning

confidence: 99%

Recent progress using the Staudinger ligation for radiolabeling applications

Mamat

Gott

Steinbach

2018

Labelled Comp Radiopharmac

View full text Add to dashboard Cite

The increasing application of positron emission tomography and single-photon emission computer tomography in radiopharmacy and nuclear medicine has stimulated the development of a multitude of novel and versatile bioorthogonal conjugation techniques. Currently, there is particular interest in radiolabeling biologically active, high molecular weight compounds like peptides, proteins, or antibodies, but also for the labeling of small organic compounds. An enormous challenge in radiolabeling these biologically active molecules is that the introduction of radiohalogens like fluorine-18 as well as various radiometals proceeds under harsh conditions, which could destroy the biomolecule. The Staudinger ligation is one of the most powerful bioorthogonal conjugation techniques. The reaction proceeds over wide temperature and pH ranges; an amide (peptide) bond is formed as the ligation unit, which minimizes distortion of the structure; no isomers are obtained; and the reaction proceeds without any metal catalyst. Due to this adaptability, this robust ligation type is a perfect candidate with a high potential for various applications in the field of radiopharmacy for the labeling of biomolecules under mild conditions. This review summarizes recent research concerning the implementation of the Staudinger ligation for radiolabeling applications.

show abstract

Section: Traceless Variant Of the Staudinger Ligationmentioning

confidence: 99%

Recent progress using the Staudinger ligation for radiolabeling applications

Mamat

Gott

Steinbach

2018

Labelled Comp Radiopharmac

View full text Add to dashboard Cite

show abstract

“…the labeling of bioactive molecules with fluorescence dyes 11 as well as radionuclides, [12][13][14] the chemoselective modification of peptides 5,15,16 and proteins, 17,18 the modification of polymers, 19 the preparation of special lactams, 20,21 or the synthesis of glycosyl amides. 22,23 The absence of cytotoxic copper salts makes the Staudinger approach interesting for potential in vitro and in vivo applications in contrast to other ligation reactions like the 1,3-dipolar Huisgen cycloaddition. [2][3][4] Organic azides, 24 which have no naturally available reaction partner, are easily available and are used as the starting material.…”

mentioning

confidence: 99%

Preparation of 4-Halobenzoate-Containing Phosphane-Based Building Blocks for Labeling Reactions Using the Traceless Staudinger Ligation

Mamat

Köckerling

2014

Synthesis

View full text Add to dashboard Cite

Functionalized phosphane-containing key building blocks were synthesized that are suitable for the labeling of biologically active molecules by the traceless Staudinger ligation. Thus, a 2-(diphenylphosphanyl)phenyl 4-stannylbenzoate building block was converted into the 4-iodobenzoate by the introduction of iodine. The traceless Staudinger ligation was used to introduce the resulting 4-iodobenzoate moiety into selected molecules of pharmacological interest. Furthermore, the labeling procedure was used to insert the 4-iodobenzoate moiety into a peptide on solid support. Finally, a convenient recovery procedure of the key phosphane building block 2-(diphenylphosphanyl)phenol from 2-(diphenylphosphoryl)phenol was evaluated.

show abstract

“…In nature, N ‐linked glycosylation of peptides occurs through the amine group of an asparagine residue, resulting in the formation of an amide bond with a β‐linkage to the sugar moiety. Synthetically, glycosyl azides have been used for the synthesis of N‐ glycosyl amides and N‐ glycosyl triazoles . Anomeric azides are configurationally and chemically more stable than glycosyl amines, thus they represent excellent starting materials for the synthesis of other N ‐glycosides in either configurations.…”

Section: Exocyclic Oxygen Replacementmentioning

confidence: 99%

Design and synthesis of glycomimetics: Recent advances

Tamburrini

Colombo

Bernardi

2019

Medicinal Research Reviews

Self Cite

View full text Add to dashboard Cite

In the past few decades, our understanding of glycan information‐encoding power has notably increased, thus leading to a significant growth also in the design and synthesis of glycomimetic probes. Combining data from multiple analytical sources, such as crystallography, nuclear magnetic resonance spectroscopy, and other biophysical methods (eg, surface plasmon resonance and carbohydrate microarrays) has allowed to shed light on the key interaction events between carbohydrates and their protein‐targets. However, the low metabolic stability of carbohydrates and their high hydrophilicity, which translates in low bioavailability, undermine their development as drugs. In this framework, the design of chemically modified analogues (called carbohydrate mimics or glycomimetics) appears as a valid alternative for the development of therapeutic agents. Glycomimetics, as structural and functional mimics of carbohydrates, can replace the native ligands in the interaction with target proteins, but are designed to show enhanced enzymatic stability and bioavailability and, possibly, an improved affinity and selectivity toward the target. In the present account, we specifically focus on the most recent advances in the design and synthesis of glycomimetics. In particular, we highlight the efforts of the scientific community in the development of straightforward synthetic procedures for the preparation of sugar mimics and in their preliminary biological evaluation.

show abstract

Stereoselective Synthesis of α‐ and β‐Glycofuranosyl Amides by Traceless Ligation of Glycofuranosyl Azides

Cited by 34 publications

References 126 publications

Recent progress using the Staudinger ligation for radiolabeling applications

Recent progress using the Staudinger ligation for radiolabeling applications

Preparation of 4-Halobenzoate-Containing Phosphane-Based Building Blocks for Labeling Reactions Using the Traceless Staudinger Ligation

Design and synthesis of glycomimetics: Recent advances

Contact Info

Product

Resources

About