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Cyclic glycopeptidomimetics through a versatile sugar-based scaffold.

Maria Altamura¹, Elisa Dragoni, Angela Simona Infantino

¹Menarini Ricerche SpA, Firenze, Italy.

Bioorganic & Medicinal Chemistry Letters

|April 28, 2009

Summary

This summary is machine-generated.

Researchers developed novel sugar-based cyclic peptidomimetics using a versatile saccharidic scaffold. This approach successfully synthesized diastereomerically pure cyclic SAA peptidomimetics, offering distinct bioactive conformations.

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Area of Science:

Medicinal Chemistry
Carbohydrate Chemistry
Peptide Chemistry

Background:

Cyclic peptidomimetics are explored for stable, bioactive conformations.
Incorporating sugar moieties, specifically pyranose rings, can induce specific turn structures in cyclic peptides.
Developing versatile scaffolds for sugar-based peptidomimetics is an ongoing challenge.

Purpose of the Study:

To report a new and versatile saccharidic scaffold for creating sugar-based peptidomimetics.
To demonstrate the successful synthesis of diastereomerically pure cyclic peptidomimetics incorporating this scaffold.

Main Methods:

Design and synthesis of a novel saccharidic scaffold.
Incorporation of the scaffold into cyclic peptide structures.
Stereoselective synthesis to achieve diastereomeric purity.

Main Results:

Successful utilization of the novel saccharidic scaffold.
Synthesis of diastereomerically pure cyclic SAA peptidomimetics (compounds 15 and 16).
Demonstration of the scaffold's ability to form distinct, bioactive conformations.

Conclusions:

The developed saccharidic scaffold is effective for synthesizing sugar-based cyclic peptidomimetics.
The synthesized compounds exhibit defined conformational properties due to the pyranose ring.
This work provides a new strategy for designing conformationally constrained glycopeptidomimetics.